CN109534975A - A kind of efficient catalytic synthetic method of 2- hydroxy benzophenone ketone compound - Google Patents

A kind of efficient catalytic synthetic method of 2- hydroxy benzophenone ketone compound Download PDF

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CN109534975A
CN109534975A CN201910006414.8A CN201910006414A CN109534975A CN 109534975 A CN109534975 A CN 109534975A CN 201910006414 A CN201910006414 A CN 201910006414A CN 109534975 A CN109534975 A CN 109534975A
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hydroxy benzophenone
tert
ketone compound
benzophenone ketone
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CN109534975B (en
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邱仁华
童舟
唐智
许智慧
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Hunan University
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    • 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
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings

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  • Organic Chemistry (AREA)
  • Furan Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

Present invention discloses a kind of 2- hydroxy benzophenone ketone compound and its green catalysis synthetic methods, this method is with benzofuranone and its derivative raw material, using nickel chloride as catalyst, toluene is solvent, di-tert-butyl peroxide is oxidant, sodium carbonate is under conditions of alkali, higher yields obtains 2- hydroxy benzophenone ketone compound.This method has the advantages that cost is relatively low, and yield is high, easy to operate, pollution-free, has potential prospects for commercial application.This method provides cheap, green a approach for the preparation of 2- hydroxybenzophenone compound.

Description

A kind of efficient catalytic synthetic method of 2- hydroxy benzophenone ketone compound
[technical field]
The invention belongs to be catalyzed organic synthesis field, a kind of height of 2- hydroxy benzophenone ketone compound is related in particular to Imitate process for catalytic synthesis.
[background technique]
2- hydroxy benzophenone ketones derivant is a kind of widely used auxiliary agent, it can absorb ultraviolet light strongly, while It is widely used in the fields such as daily-use chemical industry, medicine, pesticide, plastics, coating.ESCALOL 567 (UV 1) is made For light stabilizer.The ultraviolet light that 200~400nm can effectively be absorbed, hardly picks up visible light, can be used for painting and various plastics Product, especially suitable for light-coloured transparent product, even more good cosmetic additive agent.2,4 dihydroxyl benzophenone is ultraviolet light Absorbent is suitable for polyvinyl chloride, polystyrene, epoxy resin, celluosic resin, unsaturated-resin, coating and synthetic rubber Deng.It is also used as synthesizing the raw material of other ultraviolet absorbing agents simultaneously.
The synthetic method of 2- hydroxy benzophenone ketone compound can be divided into following several by starting material: (1) with adjacent hydroxyl Compound of benzaldehyde category is starting material；(2) using benzophenone and its derivative as starting material；(3) it is with benzoyl formic acid Starting material.Synthesizing 2- hydroxy benzophenone ketone compound as starting material using benzofuranone, there is raw material to be easy to get, operate letter Single, reaction condition is relatively mild, product yield and the advantages that purity is high, and its synthesis technology report is less.Industrial production at present Condition used in benzofuranones is harsher, complicated for operation and inefficient, still improve technique.With benzo furan Ketone of muttering is starting material, and nickel chloride is catalyst, and di-tert-butyl peroxide is oxidant, and sodium carbonate is alkali, lower pot of air Method synthesizes 2- hydroxy benzophenone ketone compound, and the method raw material is easy to get, is easy to operate, reaction condition is relatively mild, product yield And purity is high, and its synthesis technology report is less.Currently, both at home and abroad not yet about using benzofuranone as starting material, chlorine Change nickel is catalyst, and di-tert-butyl peroxide is oxidant, one pot process 2- hydroxy benzophenone ketone compound under air Open source literature and patent application.
[summary of the invention]
The purpose of the present invention is to provide one kind using nickel chloride as catalyst, and di-tert-butyl peroxide is oxidant, carbon Sour sodium is alkali, using benzofuranone as raw material, the method that efficiently synthesizes 2- hydroxy benzophenone ketone compound.This method have at The advantages that this is lower, and yield is high, easy to operate, pollution-free, for realizing that its industrialized production has certain feasibility.For up to To foregoing invention purpose, the present invention proposes technical solution below:
To achieve the above object of the invention, the present invention proposes technical solution below:
The synthetic method of a kind of 2- hydroxy benzophenone ketone compound I, wherein 2- hydroxy benzophenone ketone compound I structure Formula is as follows:
The wherein R1-R2It is selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, methoxyl group, phenyl, fluorine, chlorine, bromine；Its The green catalysis synthetic method of middle compound I, which is characterized in that be that reaction is former with benzofuranone II using nickel chloride as catalyst Material, under air conditions, 80 DEG C of effecting reactions can obtain the 2- hydroxy benzophenone ketone of higher yields within the time of 12h Close object I；
In above-mentioned synthetic method, wherein benzofuranone and its derivative I I structural formula are as follows:
The wherein R1-R2It is selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, methoxyl group, phenyl, fluorine, chlorine, bromine；
In above-mentioned synthetic method, the dosage of catalyst is 10mol%；The dosage of oxidant is two equivalents；The dosage of alkali It is two equivalents；Solvent is toluene；It is reacted under air；The reaction time is 12h, and reaction temperature is 80 DEG C.
One kind 2- hydroxy benzophenone ketone compound efficient catalytic synthetic method provided by the present invention opens new low Cost " green " approach, the advantage is that: the benzofuranone analog derivative source as raw material is more extensive, the choosing of target product Selecting property and yield are higher, and reaction condition is mild, and operation is easy.
[Detailed description of the invention]
It is the route map provided by the present invention for preparing 2- hydroxy benzophenone ketone compound shown in attached drawing.
[specific embodiment]
One kind 2- hydroxy benzophenone ketone compound efficient catalytic synthetic method provided by the present invention, refers to attached drawing: By benzofuranone derivatives, catalyst nickel chloride, oxidant di-tert-butyl peroxide, solvent toluene is placed in reaction vessel It is interior, it is reacted 12 hours under 80 DEG C of air environment, column separation obtains target product after the reaction was completed.
Below with reference to specific preparating example, the present invention will be further described:
Preparation example 1
Benzofuranone derivatives (R is added in 25mL reaction tube1=H, R2=4- methyl) 0.02mmol, chlorination is added Raney nickel 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, solvent toluene 1ml, sodium carbonate 0.04mmol, 80 12h is reacted under DEG C air.After reaction, target compound 2- hydroxy benzophenone ketone compound is obtained through column chromatography for separation (R1=H, R2=4- methyl), obtain yellow liquid, yield 99%.
Preparation example 2
Benzofuranone derivatives (R is added in 25mL reaction tube1=H, R2=H) 0.02mmol, nickel chloride catalyst is added Agent 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, solvent toluene 1ml, sodium carbonate 0.04mmol, 80 DEG C of air Lower reaction 12h.After reaction, target compound 2- hydroxy benzophenone ketone compound (R is obtained through column chromatography for separation1=H, R2 =H), obtain yellow liquid, yield 99%.
Preparation example 3
Benzofuranone derivatives (R is added in 25mL reaction tube1=H, R2=2- methyl) 0.02mmol, chlorination is added Raney nickel 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml, 80 12h is reacted under DEG C air.After reaction, target compound 2- hydroxy benzophenone ketone compound is obtained through column chromatography for separation (R1=H, R2=2- methyl), obtain yellow liquid, yield 89%.
Preparation example 4
Benzofuranone derivatives (R is added in 25mL reaction tube1=H, R2=4- ethyl) 0.02mmol, chlorination is added Raney nickel 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml, 80 12h is reacted under DEG C air.After reaction, target compound 2- hydroxy benzophenone ketone compound is obtained through column chromatography for separation (R1=H, R2=4- ethyl), obtain yellow liquid, yield 94%.
Preparation example 5
Benzofuranone derivatives (R is added in 25mL reaction tube1=H, R2=4- isopropyl) 0.02mmol, chlorine is added Change Raney nickel 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml, 12h is reacted under 80 DEG C of air.After reaction, target compound 2- hydroxy benzophenone ketone compound is obtained through column chromatography for separation (R1=H, R2=4- isopropyl), obtain yellow liquid, yield 99%.
Preparation example 6
Benzofuranone derivatives (R is added in 25mL reaction tube1=H, R2=4- tert-butyl) 0.02mmol, chlorine is added Change Raney nickel 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml, 12h is reacted under 80 DEG C of air.After reaction, target compound 2- hydroxy benzophenone ketone compound is obtained through column chromatography for separation (R1=H, R2=4- tert-butyl), obtain yellow liquid, yield 99%.
Preparation example 7
Benzofuranone derivatives (R is added in 25mL reaction tube1=H, R2=3,5- dimethyl base) 0.02mmol, add Enter nickel chloride catalyst agent 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml reacts 12h under 80 DEG C of air.After reaction, target compound 2- hydroxy benzophenone ketone is obtained through column chromatography for separation Close object (R1=H, R2=3,5- dimethyl base), obtain white solid, yield 42%.
Preparation example 8
Benzofuranone derivatives (R is added in 25mL reaction tube1=H, R2=4- methoxyl group) 0.02mmol, chlorine is added Change Raney nickel 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml, 12h is reacted under 80 DEG C of air.After reaction, target compound 2- hydroxy benzophenone ketone compound is obtained through column chromatography for separation (R1=H, R2=4- methoxyl group), obtain yellow liquid, yield 82%.
Preparation example 9
Benzofuranone derivatives (R is added in 25mL reaction tube1=H, R2=4- phenyl) 0.02mmol, chlorination is added Raney nickel 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml, 80 12h is reacted under DEG C air.After reaction, target compound 2- hydroxy benzophenone ketone compound is obtained through column chromatography for separation (R1=H, R2=4- phenyl), obtain yellow liquid, yield 78%.
Preparation example 10
Benzofuranone derivatives (R is added in 25mL reaction tube1=H, R2=4-Cl) 0.02mmol, nickel chloride is added Catalyst 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml, 80 DEG C 12h is reacted under air.After reaction, target compound 2- hydroxy benzophenone ketone compound (R is obtained through column chromatography for separation1 =H, R2=4-Cl), obtain yellow solid, yield 73%.
Preparation example 11
Benzofuranone derivatives (R is added in 25mL reaction tube1=H, R2=4-F) 0.02mmol, nickel chloride is added and urges Agent 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml, 80 DEG C of skies 12h is reacted under gas.After reaction, target compound 2- hydroxy benzophenone ketone compound (R is obtained through column chromatography for separation1= H, R2=4-F), obtain yellow liquid, yield 83%.
Preparation example 12
Benzofuranone derivatives (R is added in 25mL reaction tube1=H, R2=3- tert-butyl) 0.02mmol, chlorine is added Change Raney nickel 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml, 12h is reacted under 80 DEG C of air.After reaction, target compound 2- hydroxy benzophenone ketone compound is obtained through column chromatography for separation (R1=H, R2=3- tert-butyl), obtain yellow liquid, yield 99%.
Preparation example 13
Benzofuranone derivatives (R is added in 25mL reaction tube1=H, R2=o-tert-butyl) 0.02mmol, chlorine is added Change Raney nickel 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml, 12h is reacted under 80 DEG C of air.After reaction, target compound 2- hydroxy benzophenone ketone compound is obtained through column chromatography for separation (R1=H, R2=o-tert-butyl), obtain yellow liquid, yield 92%.
Preparation example 14
Benzofuranone derivatives (R is added in 25mL reaction tube1=4-Cl, R2=H) 0.02mmol, nickel chloride is added Catalyst 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml, 80 DEG C 12h is reacted under air.After reaction, target compound 2- hydroxy benzophenone ketone compound (R is obtained through column chromatography for separation1 =4-Cl, R2=3- tert-butyl), obtain yellow liquid, yield 80%.
Preparation example 15
Benzofuranone derivatives (R is added in 25mL reaction tube1=4-Br, R2=H) 0.02mmol, nickel chloride is added Catalyst 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml, 80 DEG C 12h is reacted under air.After reaction, target compound 2- hydroxy benzophenone ketone compound (R is obtained through column chromatography for separation1 =4-Cl, R2=3- tert-butyl), obtain yellow liquid, yield 98%.
Preparation example 16
Benzofuranone derivatives (R is added in 25mL reaction tube1=2,4- di-t-butyl, R2=2,3- dimethyl) Nickel chloride catalyst agent 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate is added in 0.02mmol 0.04mmol, solvent toluene 1ml react 12h under 80 DEG C of air.After reaction, target compound is obtained through column chromatography for separation 2- hydroxy benzophenone ketone compound (R1=2,4- di-t-butyl, R2=2,3- dimethyl), yellow solid is obtained, yield is 80%.
Preparation example 17
Benzofuranone derivatives (R is added in 25mL reaction tube1=2- methyl, R2=4- bromine) 0.02mmol, chlorine is added Change Raney nickel 10mOl%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml, 12h is reacted under 80 DEG C of air.After reaction, target compound 2- hydroxy benzophenone ketone compound is obtained through column chromatography for separation (R1=2- methyl, R2=4- bromine), obtain yellow solid, yield 99%.
Preparation example 18
Benzofuranone derivatives (R is added in 25mL reaction tube1=2,4- dimethyl, R2=4- bromine) 0.02mmol, add Enter nickel chloride catalyst agent 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml reacts 12h under 80 DEG C of air.After reaction, target compound 2- hydroxy benzophenone ketone is obtained through column chromatography for separation Close object (R1=2,4- dimethyl, R2=4- bromine), obtain yellow solid, yield 30%.
Preparation example 19
Benzofuranone derivatives (R is added in 25mL reaction tube1=2- methyl, R2=2- chlorine) 0.02mmol, chlorine is added Change Raney nickel 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml, 12h is reacted under 80 DEG C of air.After reaction, target compound 2- hydroxy benzophenone ketone compound is obtained through column chromatography for separation (R1=2- methyl, R2=2- chlorine), obtain yellow solid, yield 71%.
Preparation example 20
25mBenzofuranone derivatives (R is added in L reaction tube1=2- methyl, R2=4- chlorine) 0.02mmol, chlorine is added Change Raney nickel 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml, 12h is reacted under 80 DEG C of air.After reaction, target compound 2- hydroxy benzophenone ketone compound is obtained through column chromatography for separation (R1=2- methyl, R2=4- chlorine), obtain yellow solid, yield 99%.
Preparation example 21
Benzofuranone derivatives (R is added in 25mL reaction tube1=4- tert-butyl, R2=4- chlorine) 0.02mmol, it is added Nickel chloride catalyst agent 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml reacts 12h under 80 DEG C of air.After reaction, target compound 2- hydroxy benzophenone ketone is obtained through column chromatography for separation Close object (R1=4- tert-butyl, R2=4- chlorine), obtain yellow solid, yield 99%.
Preparation example 22
Benzofuranone derivatives (R is added in 25mL reaction tube1=4- tert-butyl, R2=2- chlorine) 0.02mmol, it is added Nickel chloride catalyst agent 10mol%, di-tert-butyl peroxide oxidant 0.04mmol, sodium carbonate 0.04mmol, solvent toluene 1ml reacts 12h under 80 DEG C of air.After reaction, target compound 2- hydroxy benzophenone ketone is obtained through column chromatography for separation Close object (R1=4- tert-butyl, R2=2- chlorine), obtain yellow solid, yield 90%.
The embodiments described above only express several embodiments of the present invention, and the description thereof is more specific and detailed, but simultaneously Limitations on the scope of the patent of the present invention therefore cannot be interpreted as.It should be pointed out that for those of ordinary skill in the art For, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to guarantor of the invention Protect range.Therefore, the scope of protection of the patent of the present invention should be wanted with appended right.

Claims (3)

1. the synthetic method of one kind 2- hydroxy benzophenone ketone compound I, wherein 2- hydroxy benzophenone ketone compound I structural formula It is as follows:
The wherein R1-R2It is selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, methoxyl group, phenyl, fluorine, chlorine, bromine；Wherein change Close the green catalysis synthetic method of object I, which is characterized in that using nickel chloride as catalyst, using benzofuranone II as reaction raw materials, Under air conditions, 80 DEG C of effecting reactions can obtain the 2- hydroxy benzophenone ketone compound I of higher yields within the time of 12h.
2. synthetic method according to claim 1, wherein simultaneously furanone II structural formula is as follows:
The wherein R1-R2It is selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, methoxyl group, phenyl, fluorine, chlorine, bromine.
3. synthetic method according to claim 1, which is characterized in that the dosage of catalyst is 10mol%；The use of oxidant Amount is two equivalents；The dosage of alkali is two equivalents；Solvent is toluene；It is reacted under air；The reaction time is 12h, reaction Temperature is 80 DEG C.
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CN111393277A (en) * 2020-03-15 2020-07-10 山西医科大学 4-butyl polyhydroxy benzophenone compound derivative and application thereof
CN113999129A (en) * 2021-11-23 2022-02-01 长沙普济生物科技股份有限公司 Synthetic method of amino acid surfactant containing phenolic hydroxyl
CN115197143A (en) * 2022-05-26 2022-10-18 湖南大学 Dinaphthoazepine, derivative thereof and nickel catalytic synthesis method thereof
CN116768709A (en) * 2023-05-30 2023-09-19 湖南大学 Efficient synthesis method of 2-hydroxy stilbene compounds

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111393277A (en) * 2020-03-15 2020-07-10 山西医科大学 4-butyl polyhydroxy benzophenone compound derivative and application thereof
CN113999129A (en) * 2021-11-23 2022-02-01 长沙普济生物科技股份有限公司 Synthetic method of amino acid surfactant containing phenolic hydroxyl
CN113999129B (en) * 2021-11-23 2023-09-01 长沙普济生物科技股份有限公司 Synthesis method of amino acid surfactant containing phenolic hydroxyl group
CN115197143A (en) * 2022-05-26 2022-10-18 湖南大学 Dinaphthoazepine, derivative thereof and nickel catalytic synthesis method thereof
CN115197143B (en) * 2022-05-26 2023-12-22 湖南大学 Dinaphtholoazepine and derivatives thereof and nickel catalytic synthesis method thereof
CN116768709A (en) * 2023-05-30 2023-09-19 湖南大学 Efficient synthesis method of 2-hydroxy stilbene compounds
CN116768709B (en) * 2023-05-30 2024-08-06 湖南大学 Efficient synthesis method of 2-hydroxy stilbene compounds

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