NO134371B - - Google Patents

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Publication number: NO134371B
Authority: NO; Norway
Prior art keywords: methyl; water; recovered; reaction mixture; dione
Prior art date: 1970-01-21

Application number

NO2098/72A

Other languages

English (en)

Norwegian (no)

Other versions

NO134371C (xx

Inventor

D R Parrish

Z G Hajos

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1970-01-21

Filing date

1972-06-13

Publication date

1976-06-21

1972-06-13 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1976-06-21 Publication of NO134371B publication Critical patent/NO134371B/no

1976-09-29 Publication of NO134371C publication Critical patent/NO134371C/no

Links

125000000217 alkyl group Chemical group 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
125000002619 bicyclic group Chemical group 0.000 claims description 3
239000000543 intermediate Substances 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 20
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 16
239000000243 solution Substances 0.000 description 14
150000001875 compounds Chemical class 0.000 description 11
239000003921 oil Substances 0.000 description 11
HXZILEQYFQYQCE-UHFFFAOYSA-N 2-methylcyclopentane-1,3-dione Chemical compound CC1C(=O)CCC1=O HXZILEQYFQYQCE-UHFFFAOYSA-N 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
238000009835 boiling Methods 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
-1 m-methoxybenzyl Chemical group 0.000 description 7
239000012071 phase Substances 0.000 description 7
JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000012230 colorless oil Substances 0.000 description 6
239000012043 crude product Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
238000004508 fractional distillation Methods 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
YDFBIBUYOUFJMR-UHFFFAOYSA-N 2-ethylcyclopentane-1,3-dione Chemical compound CCC1C(=O)CCC1=O YDFBIBUYOUFJMR-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
WRKGBXKSAFJPMA-UHFFFAOYSA-N 2-ethyl-2-(3-oxobutyl)cyclopentane-1,3-dione Chemical compound CC(=O)CCC1(CC)C(=O)CCC1=O WRKGBXKSAFJPMA-UHFFFAOYSA-N 0.000 description 2
ZNVNGGMKNCURSF-UHFFFAOYSA-N 2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione Chemical compound CC(=O)CCC1(C)C(=O)CCCC1=O ZNVNGGMKNCURSF-UHFFFAOYSA-N 0.000 description 2
OZBYSCPBJGAYMQ-UHFFFAOYSA-N 2-methyl-2-(3-oxobutyl)cyclopentane-1,3-dione Chemical compound CC(=O)CCC1(C)C(=O)CCC1=O OZBYSCPBJGAYMQ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
238000000034 method Methods 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
RFCLQVSOHWJXEU-UHFFFAOYSA-N 2-[6-(3-methoxyphenyl)-3-oxohexyl]-2-methylcyclopentane-1,3-dione Chemical compound COC1=CC=CC(CCCC(=O)CCC2(C)C(CCC2=O)=O)=C1 RFCLQVSOHWJXEU-UHFFFAOYSA-N 0.000 description 1
ZQYLUOYVHHWICM-UHFFFAOYSA-N 2-butyl-2-(3-oxobutyl)cyclohexane-1,3-dione Chemical compound C(CCC)C1(C(CCCC1=O)=O)CCC(C)=O ZQYLUOYVHHWICM-UHFFFAOYSA-N 0.000 description 1
YMQRPZZAFLGYQY-UHFFFAOYSA-N 2-butylcyclohexane-1,3-dione Chemical compound CCCCC1C(=O)CCCC1=O YMQRPZZAFLGYQY-UHFFFAOYSA-N 0.000 description 1
JTRQSSRXYULBAA-UHFFFAOYSA-N 2-ethyl-2-(3-oxobutyl)cyclohexane-1,3-dione Chemical compound CC(=O)CCC1(CC)C(=O)CCCC1=O JTRQSSRXYULBAA-UHFFFAOYSA-N 0.000 description 1
CBYSZLTXXOKQQO-UHFFFAOYSA-N 2-ethylcyclohexane-1,3-dione Chemical compound CCC1C(=O)CCCC1=O CBYSZLTXXOKQQO-UHFFFAOYSA-N 0.000 description 1
QDQKCEIOMJUGKJ-UHFFFAOYSA-N 2-methyl-2-(3-oxopentyl)cyclopentane-1,3-dione Chemical compound CCC(=O)CCC1(C)C(=O)CCC1=O QDQKCEIOMJUGKJ-UHFFFAOYSA-N 0.000 description 1
VSGJHHIAMHUZKF-UHFFFAOYSA-N 2-methylcyclohexane-1,3-dione Chemical compound CC1C(=O)CCCC1=O VSGJHHIAMHUZKF-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
NHMJKYVPXYBHSL-UHFFFAOYSA-N 3-hydroxy-2-methylcyclohex-2-en-1-one Chemical compound CC1=C(O)CCCC1=O NHMJKYVPXYBHSL-UHFFFAOYSA-N 0.000 description 1
QREBEZZOILCJEP-UHFFFAOYSA-N 6-(3-methoxyphenyl)hex-1-en-3-one Chemical compound COC1=CC=CC(CCCC(=O)C=C)=C1 QREBEZZOILCJEP-UHFFFAOYSA-N 0.000 description 1
239000012027 Collins reagent Substances 0.000 description 1
239000003810 Jones reagent Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
NKRNGKIEDAVMHL-UHFFFAOYSA-L dihydroxy(dioxo)chromium;pyridine Chemical compound O[Cr](O)(=O)=O.C1=CC=NC=C1 NKRNGKIEDAVMHL-UHFFFAOYSA-L 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000005837 enolization reaction Methods 0.000 description 1
MGPSIDGTLFKDEY-UHFFFAOYSA-N ethyl 5-oxohexanoate Chemical compound CCOC(=O)CCCC(C)=O MGPSIDGTLFKDEY-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002035 hexane extract Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
IMTFKLOKSJDBIM-UHFFFAOYSA-N methyl 7-(1-methyl-2,5-dioxocyclopentyl)-5-oxoheptanoate Chemical compound COC(=O)CCCC(=O)CCC1(C)C(=O)CCC1=O IMTFKLOKSJDBIM-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/73—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with hydrogenation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/487—Saturated compounds containing a keto group being part of a ring containing hydroxy groups
- C07C49/507—Saturated compounds containing a keto group being part of a ring containing hydroxy groups polycyclic
- C07C49/513—Saturated compounds containing a keto group being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Catching Or Destruction (AREA)

NO2098/72A 1970-01-21 1972-06-13 NO134371C (xx)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US476270A	1970-01-21	1970-01-21

Publications (2)

Publication Number	Publication Date
NO134371B true NO134371B (xx)	1976-06-21
NO134371C NO134371C (xx)	1976-09-29

Family

ID=27421984

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
NO200/71A NO134983C (xx)	1970-01-21	1971-01-20
NO2099/72A NO138000C (no)	1970-01-21	1972-06-13	Fremgangsmaate for fremstilling av 19-nortestosteron og 19-nor-9beta, 10alfa-testosteron henholdsvis 17beta-tert.-butyleter derav
NO2098/72A NO134371C (xx)	1970-01-21	1972-06-13
NO761104A NO761104L (xx)	1970-01-21	1976-03-30

Family Applications Before (2)

Application Number	Title	Priority Date	Filing Date
NO200/71A NO134983C (xx)	1970-01-21	1971-01-20
NO2099/72A NO138000C (no)	1970-01-21	1972-06-13	Fremgangsmaate for fremstilling av 19-nortestosteron og 19-nor-9beta, 10alfa-testosteron henholdsvis 17beta-tert.-butyleter derav

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO761104A NO761104L (xx)	1970-01-21	1976-03-30

Country Status (21)

Country	Link
US (2)	US3975440A (xx)
JP (2)	JPS5737573B1 (xx)
AT (4)	AT308087B (xx)
BE (1)	BE761783A (xx)
CA (2)	CA993878A (xx)
CH (3)	CH588434A5 (xx)
DE (3)	DE2102623C2 (xx)
DK (2)	DK146717C (xx)
ES (2)	ES387449A1 (xx)
FI (2)	FI53450C (xx)
FR (2)	FR2077253B1 (xx)
GB (2)	GB1325632A (xx)
HU (2)	HU166419B (xx)
IE (3)	IE35093B1 (xx)
IL (1)	IL35985A (xx)
NL (2)	NL164267C (xx)
NO (4)	NO134983C (xx)
PH (2)	PH12661A (xx)
SE (2)	SE393798B (xx)
YU (1)	YU35332B (xx)
ZA (1)	ZA7120B (xx)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4201869A (en) *	1970-12-21	1980-05-06	Hoffmann-La Roche Inc.	Intermediates for steroid total synthesis process utilizing asymmetric induction
ZA814972B (en) *	1980-07-30	1982-07-28	Beecham Group Plc	Reduced naphthalenes,their preparation and use

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2668858A (en) *		1954-02-09		Process for their preparation
US2407673A (en) *	1941-06-20	1946-09-17	Research Corp	Process for the synthesis of 1-keto-8-methylhexahydroindanol-1
US2833694A (en) *	1955-08-25	1958-05-06	Ciba Pharm Prod Inc	Process for splitting racemates
NL130309C (xx) *	1963-11-29
NL131552C (xx) *	1965-04-28
AT278767B (de) *	1965-10-13	1970-02-10	Hoffmann La Roche	Verfahren zur herstellung von neuen indanderivaten
US3501479A (en) *	1967-05-19	1970-03-17	American Cyanamid Co	Dihydroquinolines and substituted dihydroquinolines and method of preparing the same
US3897460A (en) *	1968-10-04	1975-07-29	Hoffmann La Roche	3{62 -Tertiarybutoxy-decahydro-benz{8 E{9 indenes
DE2016750A1 (de) *	1970-04-04	1971-10-14	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Verfahren zur Herstellung von 2,2 disubstituierten Cycloalkan 1,3 dionen

1970
- 1970-12-09 US US05/096,597 patent/US3975440A/en not_active Expired - Lifetime
1971
- 1971-01-04 ZA ZA710020A patent/ZA7120B/xx unknown
- 1971-01-07 CH CH18571A patent/CH588434A5/xx not_active IP Right Cessation
- 1971-01-07 CH CH638775A patent/CH597129A5/xx not_active IP Right Cessation
- 1971-01-10 PH PH12122A patent/PH12661A/en unknown
- 1971-01-12 IL IL35985A patent/IL35985A/xx unknown
- 1971-01-14 IE IE42/71A patent/IE35093B1/xx unknown
- 1971-01-14 IE IE1797/73A patent/IE35095B1/xx unknown
- 1971-01-14 IE IE1796/73A patent/IE35094B1/xx unknown
- 1971-01-19 YU YU117/71A patent/YU35332B/xx unknown
- 1971-01-19 GB GB4688172A patent/GB1325632A/en not_active Expired
- 1971-01-19 GB GB257171A patent/GB1325631A/en not_active Expired
- 1971-01-20 AT AT45571A patent/AT308087B/de active
- 1971-01-20 FI FI152/71A patent/FI53450C/fi active
- 1971-01-20 AT AT392372A patent/AT316533B/de not_active IP Right Cessation
- 1971-01-20 NO NO200/71A patent/NO134983C/no unknown
- 1971-01-20 DE DE2102623A patent/DE2102623C2/de not_active Expired
- 1971-01-20 AT AT392272A patent/AT315142B/de not_active IP Right Cessation
- 1971-01-20 ES ES387449A patent/ES387449A1/es not_active Expired
- 1971-01-20 FR FR717101825A patent/FR2077253B1/fr not_active Expired
- 1971-01-20 DE DE2166994A patent/DE2166994C3/de not_active Expired
- 1971-01-20 BE BE761783A patent/BE761783A/xx not_active IP Right Cessation
- 1971-01-20 DE DE19712166993 patent/DE2166993A1/de active Pending
- 1971-01-21 JP JP177971A patent/JPS5737573B1/ja active Pending
- 1971-01-21 HU HUHO1647A patent/HU166419B/hu unknown
- 1971-01-21 DK DK25571A patent/DK146717C/da not_active IP Right Cessation
- 1971-01-21 CA CA103,278A patent/CA993878A/en not_active Expired
- 1971-01-21 NL NL7100813.A patent/NL164267C/xx not_active IP Right Cessation
- 1971-01-21 HU HUHO1349A patent/HU166411B/hu unknown
- 1971-01-21 SE SE7100704A patent/SE393798B/xx unknown
- 1971-09-08 ES ES394882A patent/ES394882A1/es not_active Expired
- 1971-11-05 FR FR717139725A patent/FR2112170B1/fr not_active Expired
1972
- 1972-05-05 AT AT392472A patent/AT348150B/de not_active IP Right Cessation
- 1972-06-13 NO NO2099/72A patent/NO138000C/no unknown
- 1972-06-13 NO NO2098/72A patent/NO134371C/no unknown
1973
- 1973-12-28 SE SE7317592A patent/SE404607B/xx unknown
1975
- 1975-08-04 PH PH17445A patent/PH11206A/en unknown
1976
- 1976-01-07 CH CH1535676A patent/CH589024A5/xx not_active IP Right Cessation
- 1976-03-04 CA CA247,076A patent/CA1013752A/en not_active Expired
- 1976-03-30 NO NO761104A patent/NO761104L/no unknown
1977
- 1977-05-23 FI FI771632A patent/FI771632A/fi not_active Application Discontinuation
- 1977-11-11 JP JP13556877A patent/JPS5373541A/ja active Granted
1978
- 1978-06-12 US US05/914,840 patent/US4189447A/en not_active Expired - Lifetime
1979
- 1979-07-16 DK DK298479A patent/DK298479A/da not_active Application Discontinuation
- 1979-10-02 NL NL7907334A patent/NL7907334A/nl unknown

Also Published As

Publication number	Publication date
NO134371C (xx)	1976-09-29
FR2112170A1 (xx)	1972-06-16
AT315142B (de)	1974-05-10
NL7100813A (xx)	1971-07-23
PH12661A (en)	1979-07-11
HU166419B (xx)	1975-03-28
IE35094B1 (en)	1975-11-12
SE404607B (sv)	1978-10-16
JPS5373541A (en)	1978-06-30
CH597129A5 (xx)	1978-03-31
GB1325631A (en)	1973-08-08
ZA7120B (en)	1971-10-27
NO761104L (xx)	1971-07-22
IL35985A0 (en)	1971-03-24
FI53450C (fi)	1978-05-10
DE2102623C2 (de)	1982-04-15
IL35985A (en)	1974-05-16
FI771632A (xx)	1977-05-23
JPS5737573B1 (xx)	1982-08-10
YU35332B (en)	1980-12-31
IE35095B1 (en)	1975-11-12
DE2166994A1 (de)	1977-07-14
NL7907334A (nl)	1980-01-31
NL164267C (nl)	1980-12-15
FR2077253B1 (xx)	1973-06-08
FR2112170B1 (xx)	1973-06-29
NL164267B (nl)	1980-07-15
US3975440A (en)	1976-08-17
AT308087B (de)	1973-06-25
AT316533B (de)	1974-07-10
ATA392472A (de)	1978-06-15
HU166411B (xx)	1975-03-28
IE35093L (en)	1971-07-21
AT348150B (de)	1979-01-25
PH11206A (en)	1977-10-28
SE393798B (sv)	1977-05-23
NO138000B (no)	1978-02-27
NO138000C (no)	1978-06-07
DE2102623A1 (xx)	1971-07-29
BE761783A (fr)	1971-07-20
CH588434A5 (xx)	1977-05-31
JPS5546377B2 (xx)	1980-11-22
FI53450B (xx)	1978-01-31
CA1013752A (en)	1977-07-12
DE2166993A1 (de)	1977-07-14
FR2077253A1 (xx)	1971-10-22
ES394882A1 (es)	1974-03-01
NO134983C (xx)	1977-01-26
IE35093B1 (en)	1975-11-12
GB1325632A (en)	1973-08-08
DK298479A (da)	1979-07-16
US4189447A (en)	1980-02-19
ES387449A1 (es)	1974-12-16
NO134983B (xx)	1976-10-11
CH589024A5 (xx)	1977-06-30
DK146717B (da)	1983-12-12
DK146717C (da)	1984-05-21
DE2166994B2 (de)	1980-01-31
DE2166994C3 (de)	1980-10-09
CA993878A (en)	1976-07-27
YU11771A (en)	1980-06-30

Publication	Publication Date	Title
Kingsbury et al.	1960	Studies in Stereochemistry. XXXII. Mechanism of Elimination of Sulfoxides1
Cram et al.	1956	Macro Rings. XIII. Synthesis and Properties of 1, 7-Cyclododecadiyne and Related Compounds1
Windholz et al.	1963	Total synthesis of 19-norsteroids. I. d, l-Estrone methyl ether
US3029287A (en)	1962-04-10	Preparation of unsaturated ketones
Akhtar et al.	1965	Some Radical Exchange Reactions during Nitrite Ester Photolysis1
Gardner	1956	Organic Peracid Oxidation of Some Enol Esters Involving Rearrangement1
US4161480A (en)	1979-07-17	Intermediates for the synthesis of 4-demethoxydaunorubicin
US3941828A (en)	1976-03-02	Process for the preparation of cyclic ketones
Krubiner et al.	1968	Studies in the 21-methyl steroid series. Organoborane rearrangements and a novel synthesis of 21-methyl-19-norsteroids
NO134371B (xx)	1976-06-21
US3954794A (en)	1976-05-04	Heterocyclic compounds
US3816536A (en)	1974-06-11	2-2-disubstituted cycloalkane-1,3-diones
Jacobs et al.	1958	A-Nor-Δ3 (5)-cholesten-2-one1
Tarbell et al.	1954	A Rearrangement Involving Aromatization. The Condensation of Δ4-Tetrahydrophthalaldehyde with Diethyl Acetonedicarboxylate1
US4124642A (en)	1978-11-07	6,6,7-Trimethyl-tricyclo[5.2.2.01,5 ]undec-8-en-2-one
Elks	1954	Studies in the synthesis of cortisone. Part VI. Conjugated trienones derived from ergosterol
US3975442A (en)	1976-08-17	2-Alkyl-2-(3-oxoalkyl)-1,3-cyclopentadiones
Goldblum et al.	1977	Sodium chromate oxidation of enol benzoates. Allylic oxidation versus a novel rearrangement
Suzuki	1962	Studies on Fluorene Derivatives. XV. The Clemmensen Reduction of Fluorenone
US3712928A (en)	1973-01-23	Phenylcyclohexane derivatives and methods for their manufacture
DRAKE et al.	1939	A new synthesis of picene
US4110380A (en)	1978-08-29	Asymmetric synthesis of organic compounds
Suginome et al.	1988	Photoinduced molecular transformations. Part 98. The photochemistry of steroidal 6-membered cyclic. ALPHA.-nitro ketones.
Peet et al.	1973	Photochemical and acid-catalyzed rearrangements of tricyclo [4.4. 2.0] dodecanones
Vingiello et al.	1965	7-Phenyldibenz [a, h] anthracene and Benzo [e] naphtho [1, 2-b] pyrene1, 2