CN101704724B - Novel method for preparing high-proportion trans, trans-4-(4'-alkyl cyclohexyl) cyclohexyl alcohol liquid crystal intermediate compound - Google Patents
Novel method for preparing high-proportion trans, trans-4-(4'-alkyl cyclohexyl) cyclohexyl alcohol liquid crystal intermediate compound Download PDFInfo
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Abstract
The invention relates to a method for preparing a high-proportion trans, trans-4-(4'-alkyl cyclohexyl) cyclohexyl alcohol liquid crystal intermediate compound. The method comprises the following steps of: dissolving trans-4-alkyl cyclohexyl cyclohexyl ketone in an organic solvent (A); dissolving reductant boron hydride in an organic solvent (B); mixing the two obtained mixed solution; carrying out reduction reaction; carrying out transposition reaction by using Lewis acid; then carrying out acid hydrolysis; carrying out extraction by using a solvent; merging organic phases; washing the solution until the pH value is 7; adding desiccant to dry obtained products; removing the desiccant by filtration; and removing the solvent under low vacuum to obtain the high-proportion trans, trans-4-(4'-alkyl cyclohexyl) cyclohexyl alcohol liquid crystal intermediate compound. The method is simple in process and high in yield, and is favorable for realizing scale production.
Description
Technical field
The present invention relates to a kind of novel preparation method of liquid crystal intermediates compound, relate more specifically to the novel preparation method of trans, trans-4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound, belong to the compound preparing technical field.
Background technology
Thin Film Transistor-LCD (TFT-LCD) is most important a kind of in the liquid-crystal display (LCD), its output value and influence power are occupied very important status in liquid-crystal display family, be widely used in all respects such as televisor, notebook computer, watch-dog, mobile phone, and now, LCD TV has become the main flow in market.
Liquid crystal material is one of several large materials that consist of by liquid-crystal display (LCD), and liquid crystal material is being played the part of very important role therein, and is accompanied by the difference of display format, and required liquid crystal material is also different.In order to satisfy the needed individual features of various liquid crystal display devices, liquid crystal material need to mix the liquid crystalline cpd that uses about 20 kinds of different performances usually, and this just requires to have good mutual solubility between the liquid crystalline cpd, particularly at low temperatures.
Shortening the time of response and reducing energy consumption is people's unremitting pursue always.Simultaneously, we know that there is following relationship the time of response (t) with rotary viscosity (γ) and box thick (d): t ∝ γ d
2Therefore, for satisfy people aspect the video to the pursuit of dynamic menu, overcome the drawback of dynamic menu conditions of streaking, people mostly adopt in liquid crystal material, the adding viscosity-depression agent reaches the method that reduces liquid crystal material rotary viscosity (γ) and realizes shortening the time of response (t), improve the purpose of response speed, this is one of a kind of very effective approach.
So-called liquid crystal material viscosity-depression agent also is take liquid crystalline cpd as main mostly, has the individual features of liquid crystal material.Mainly comprise alkyl bis cyclohexane ethers, alkyl dicyclic hexane, alkyl dicyclohexyl vinyl, alkyl-cyclohexyl to alkyl benzene, alkyl-cyclohexyl phenylate class, alkyl-cyclohexyl to several classes such as fluorobenzene classes.At WO99/21816, WO91/16399, US6,210,760, US6,348,244, US4,868,341 and EP0, all mention in 315,050 several patents: in liquid crystal material composition, used alkyl bis cyclohexane ethers viscosity-depression agent (general formula code name: CCH) realize reducing system viscosity, to reach the purpose that realize to improve response speed, adapt to the demand of the aspect of performance that TFT-LCD and STN-LCD improve constantly liquid crystal material.Equally, at Angew.Chem.Int.Ed.2000,39, P:4216-4235 has also reported the article of Peer Kirsch andMatthias Bremer: Nematic Liquid Crystals for Active MatrixDisplays:Molecular Design and Synthesis.Also mention therein the applicable cases in TFT-LCD such as alkyl bis cyclohexane ethers, alkyl dicyclic hexane, alkyl dicyclohexyl vinyl, alkyl-cyclohexyl phenylate class, alkyl-cyclohexyl fluorobenzene class.
Patent US4,868,341, all point out among clear 60-54333 and the clear 60-69049: trans, trans-4 (4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound is a kind of important intermediate of synthesis of alkyl bis cyclohexane ethers monomer liquid crystal compound, and it Williamson's building-up reactions (WilliamsonSynthesis) occurs prepares a series of alkyl bis cyclohexane ethers monomer liquid crystal compounds.Alkyl bis cyclohexane ethers liquid crystalline cpd has many advantageous properties, as: (Δ n) is little for the optics anisotropic, and viscosity is lower, fast response time, and chemical stability is good, and good light stability, low temperature mutual solubility are good etc.Therefore, alkyl bis cyclohexane ethers liquid crystalline cpd becomes indispensable effective constituent in the medium-to-high grade liquid crystal material (as: STN, TFT) day by day.
We know, exploitation preparation alkyl bis cyclohexane ethers liquid crystalline cpd just be unable to do without trans, trans alkyl bis cyclohexane alcohol liquid crystal intermediate, and at present, generally be to be raw material by adopting trans cyclohexyl phenol, under catalyst, hydrogenation obtains cis, the mixture of trans alkyl dicyclohexyl alcohol (take cis as main)-----Yang Yongzhong, Liu Hong, Gao Renxiao has relevant report in " synthetic chemistry " the 06th phase of the 12nd volume in 2004, and then, carrying out repeatedly recrystallization can obtain a small amount of trans, trans alkyl bis cyclohexane alcohol liquid crystal intermediates, yield is only about 20%! This is the main path that obtains at present trans, trans-4 (4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound, its cis that obtains, trans alkyl dicyclohexyl alcohol mixture only are the middle transition things (that is: cis, trans alkyl dicyclohexyl alcohol mixture adopt chromic acid, potassium permanganate or clorox to carry out oxidation again and obtain alkyl dicyclohexyl ketone, and this is the classical way that several years ago prepares alkyl dicyclohexyl ketone) that the alkyl dicyclohexyl ketone of very big market demand is arranged for the oxidation preparation.
Because this method prepares alkyl dicyclohexyl ketone and exists environmental pollution, under the overall background of current common people's attaching importance to environmental protection, appealing green production, people have abandoned the route that adopts phenol system alcohol, reoxidizes ketone processed, prepare alkyl dicyclohexyl ketone and adopted single stage method to carry out selective reduction.At patent US 6,215,028 and EP 0,913,376 report is just arranged.One-step technology ketone processed, not only yield is high, and product quality is high, and, environmental protection, pollution-free, this has become the main method of present preparation alkyl dicyclohexyl ketone.So, originally adopting the mixture of cis, trans alkyl dicyclohexyl alcohol to carry out recrystallization, to obtain the approach of trans, trans alkyl bis cyclohexane alcohol liquid crystal intermediates just disconnected, this just require we must reselect obtain by way of.
At patent US 4,629, having mentioned alkyl-cyclohexyl ketone in 581 reacts in the presence of metallic lithium, liquefied ammonia, ethanol, hydrolysis can obtain trans alkyl cyclohexane alcohol again---a reaction formula is only arranged, there is no the detailed digital of yield, according to its former pair of listed material analysis, reaction should be carried out about-50 degree, and liquefied ammonia also will have the equipment that recycles and reuses, therefore, implement comparatively difficulty, be unfavorable for realizing industrialization production, simultaneously, also there is no the preparation problem of the hexamethylene alkanol of mentioning trans dicyclo in the literary composition.
Summary of the invention
The object of the invention is to overcome above-mentioned the deficiencies in the prior art; provide a kind of new preparation a high proportion of trans, trans-method of 4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound; the method technique is simple, and yield is high, is conducive to realize the large production of mass-producing.
Of the present invention trans, trans-4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound, have the structure shown in the general formula (I):
Wherein:
R is C
1-C
10Alkyl; Further, R is preferably C
1-C
10Straight chained alkyl;
More preferably, R C more preferably
1-C
7Straight chained alkyl;
Most preferably, R is-CH
3,-C
2H
5,-C
3H
7,-C
4H
9Or-C
5H
11,-C
7H
15
For realizing purpose of the present invention, provide a kind of trans, trans-novel preparation method of 4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound general formula (I), its synthetic route is as follows:
(I) (take trans as main)
Concrete preparation method's step of general formula (I) is as follows:
The trans-4-alkyl-cyclohexyl cyclohexyl ketone is dissolved in the organic solvent (A), borane reducing agent hydride dissolves in the organic solvent (B), two kinds of mixing solutionss of gained are mixed, carry out reduction reaction, adopt again Lewis acid to carry out translocation reaction, then carry out acidic hydrolysis, extract with solvent again, merge organic phase, be washed to neutrality, products therefrom is added siccative carry out drying, the filtering siccative, under the rough vacuum, remove solvent, can obtain a high proportion of trans, trans-4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound (trans accounting for more than 90%).
For obtaining high purity product, carry out recrystallization with organic solvent again, can obtain purity 99.8% highly purified trans, trans-4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound.
Among the preparation method of the present invention, described organic solvent A, B all can adopt at least a in the following material: ethanol, methyl alcohol, Virahol, 1,4-diox, tetrahydrofuran (THF), methyltetrahydrofuran, acetone, butanone, it is preferably ethanol, methyl alcohol, Virahol, acetone, butanone, tetrahydrofuran (THF), more preferably ethanol, tetrahydrofuran (THF), most preferably being organic solvent A is that tetrahydrofuran (THF), organic solvent B are ethanol.
Among the preparation method of the present invention, described hydroborate preferably adopts sodium borohydride or POTASSIUM BOROHYDRIDE.
Among the preparation method of the present invention, described hydrolysis is implemented in the presence of acid, preferred randomly hydrochloric acid, sulfuric acid, ammonium chloride, the glacial acetic acid of dilute with water, more preferably hydrochloric acid, the most preferably mixture of hydrochloric acid and water.
Preparation method of the present invention can implement in relatively wide temperature range.Typical temperature is-10 ℃ to 80 ℃, preferred-5 ℃ to 70 ℃, more selects 0 ℃ to 50 ℃.Most preferably be in the preparation process, the reaction of each reactive component is carried out reduction reaction under 0 ℃ to 40 ℃, then, is hydrolyzed under 10 ℃ at 0 ℃ again.
Preparation method of the present invention, the reaction times is not crucial, can how much selecting in wider scope according to production lot.Generally speaking, each step reaction combines and reaches 10 hours most, and preferably the longest is 8 hours, and most preferably the longest is 6 hours.
Preparation method of the present invention, in the best was implemented, for the trans-4-alkyl-cyclohexyl cyclohexyl ketone (A) of 1mol, employed borane reducing agent hydride was generally 0.1mol to 1.5mol, be preferably 0.2mol to 1.1mol, more preferably 0.4mol to 0.7mol; Employed organic solvent A (as: tetrahydrofuran (THF)) is that 300-700ml, employed organic solvent B (as: ethanol) are 400-1000ml; Employed Lewis acid is generally 0.1mol to 2.0mol, and more preferably 0.6mol to 1.5mol most preferably is 0.8mol to 1.2mol.
Among the preparation method of the present invention, extract used solvent and can adopt at least a in the following solvent: toluene, ethyl acetate, methylene dichloride.
Among the preparation method of the present invention, carry out the used organic solvent of last recrystallization and be at least a in the following material: ethanol, methyl alcohol, Virahol, acetone, butanone, ethyl acetate, toluene, methylene dichloride, be preferably ethanol, methyl alcohol, Virahol, butanone, ethyl acetate, more preferably ethanol, methyl alcohol, Virahol, ethyl acetate most preferably are the mixture of two of ethanol, methyl alcohol or ethanol and methyl alcohol.
Among the preparation method of the present invention, the multiple that carries out the used organic solvent of last recrystallization is very crucial.For 1 times product, the employed organic solvent of recrystallization is generally 0.5 times to 5.0 times, is preferably 0.6 times to 3.0 times, more preferably 1.0 times to 2.7 times, most preferably is 1.2 times to 2.0 times.
The present invention be directed to the deficiency of trans, the trans alkyl bis cyclohexane alcohol of existing preparation, adopting alkyl dicyclohexyl ketone is raw material, selected employing hydroborate/organic solvent A/organic solvent B reduction system reducing, adopt Lewis acid to carry out transposition, and then carry out the series of steps such as acidic hydrolysis, made at last the trans at high proportion alkyl bis cyclohexane alcohol liquid crystal intermediates that accounts for more than 90%.Preparation method's technique of the present invention is simple, and yield is high, and yield reaches more than 80%, and further behind the recrystallization, its product purity can reach more than 99.8%, and fusing point reaches more than 41 ℃.Technique of the present invention has reached the degree of very optimizing, and the by product in the product is down to technique acceptable degree such as the amount of: cis-4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohol and other impurity.The synthetic route of the present invention's design is unique; operational path is shorter; processing condition are reasonable; treatment process is suitable; product quality is excellent; be conducive to realize the large production of mass-producing, can satisfy STN-LCD and TFT-LCD to liquid crystal intermediates high purity, high-quality requirement, to adapt to STN-LCD and TFT-LCD with the needs of liquid crystal material fast development.
Embodiment
The present invention is described further below in conjunction with specific embodiment, yet described embodiment should not explain in the mode of restriction.
Embodiment 1:
Present embodiment is the preparation (I-1) of trans, trans-4-(4 '-propyl group cyclohexyl) cyclohexyl alcohol:
In there-necked flask, add 44.4g (0.2mol) trans-4-propyl group cyclohexyl ring hexyl ketone, 120ml tetrahydrofuran (THF) (organic solvent A), and agitator, constant pressure funnel, thermometer be installed, the there-necked flask outside lowers the temperature with icy salt solution, the solution that adds 5.7g (0.15mol) sodium borohydride and 100ml dehydrated alcohol (organic solvent B) in the constant pressure funnel, temperature control is below 5 ℃, begin to drip the solution of sodium borohydride and dehydrated alcohol, approximately drip one hour, finish, insulation reaction is 3 hours again; When temperature is 0 ℃, add rapidly the mixture of 26.7g (0.2mol) aluminum chloride and 200ml methylene dichloride, at 0 ℃--5 ℃ of translocation reactions 2 hours; Drip the solution of 20ml hydrochloric acid and 50ml water in the reaction solution, temperature control stirs and is hydrolyzed 20 minutes below 10 ℃; With the saturated aqueous sodium carbonate neutralization, separatory with 100ml * 2 toluene aqueous phase extracted, merges organic phase, and is extremely neutral with 300ml * 3 water washings again; Use anhydrous MgSO
4Dry; The filtering siccative carries out rough vacuum decompression (0.01Mpa) evaporate to dryness, removes solvent, makes crude product; Use respectively again the dehydrated alcohol recrystallization secondary of 80mL, 60mL, make white crystal product 38.1g.Gas product chromatography purity assay 〉=99.8%, the product fusing point is: 41.8 ℃, product yield is 85%.
Embodiment 2:
Present embodiment is the preparation (I-1) of trans, trans-4-(4 '-propyl group cyclohexyl) cyclohexyl alcohol:
Preparation process is with embodiment 1, and difference is: with the sodium borohydride reduction agent in the POTASSIUM BOROHYDRIDE alternate embodiment 1, prepare target product (I-1).
Experimental result is as follows: the product fusing point is: 41.8 ℃, purity 〉=99.8%, product yield are 83%.
Embodiment 3:
Present embodiment is the preparation (I-2) of trans, trans-4-(4 '-amyl group cyclohexyl) cyclohexyl alcohol:
Preparation process is with embodiment 1, and difference is: with in trans-4-amyl group cyclohexyl ring hexyl ketone alternate embodiment 1 trans-4-propyl group cyclohexyl ring hexyl ketone raw material, prepare target product (I-2).
Experimental result is as follows: the product fusing point is: 45.3 ℃, purity 〉=99.8%, product yield are 86%.
Embodiment 4:
Present embodiment is the preparation (I-3) of trans, trans-4-(4 '-butyl cyclohexyl) cyclohexyl alcohol:
Preparation process is with embodiment 1, and difference is: with in trans-4-butyl cyclohexyl ring hexyl ketone alternate embodiment 1 trans-4-propyl group cyclohexyl ring hexyl ketone raw material, prepare target product (I-3).
Experimental result is as follows: the product fusing point is: 44.3 ℃, purity 〉=99.8%, product yield are 85%.
Embodiment 5:
Present embodiment is the preparation (I-4) of trans, trans-4-(4 '-ethyl cyclohexyl) cyclohexyl alcohol:
Preparation process is with embodiment 1, and difference is: with in trans-4-ethyl cyclohexyl ring hexyl ketone alternate embodiment 1 trans-4-propyl group cyclohexyl ring hexyl ketone raw material, prepare target product (I-4).
Experimental result is as follows: the product fusing point is: 57.3 ℃, purity 〉=99.8%, product yield are 87%.
The comparison for preparing target product and embodiment 1 according to existing preparation method:
Press Yang Yongzhong, Liu Hong, Gao Renxiao in the method for " synthetic chemistry " the 12nd volume in 2004 the 06th interim report, be prepared trans, trans-4-(4 '-propyl group cyclohexyl) cyclohexyl alcohol (I-1).Be raw material by adopting trans cyclohexyl phenol, under Raney Ni catalyst, hydrogenation obtains the mixture of cis, trans alkyl dicyclohexyl alcohol (take cis as main, cis accounts for 55%), carry out recrystallization four times with 3.5 times, 3.0 times, 2.0 times, 1.5 times ethanol respectively again, obtain target product---trans, trans-4-(4 '-the propyl group cyclohexyl) cyclohexyl alcohol (I-1), its gas chromatograph purity assay is 99.5%, the product shows white crystal, melting point compound: 38.9 ℃.Yield is 19%.
This shows adopt method preparation of the present invention trans, trans-4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound, not only yield is high than prior art, and purity is high, the product fusing point is high.
Application examples:
According to patent US4, the method for mentioning in 868,341, prepare a series of alkyl bis cyclohexane ethers liquid crystalline cpds:
1) anti-, anti--4-methoxyl group-4 '-the propyl group bis cyclohexane, M.P.9.4 ℃, C.P18.2 ℃.
2) anti-, anti--4-methoxyl group-4 '-the butyl bis cyclohexane, M.P.7.5 ℃, C.P27.8 ℃.
3) anti-, anti--4-methoxyl group-4 '-the amyl group bis cyclohexane, M.P.12.1 ℃, C.P36.5 ℃.
4) anti-, anti--4-oxyethyl group-4 '-the propyl group bis cyclohexane, M.P.49.0 ℃.
5) anti-, anti--4-oxyethyl group-4 '-the butyl bis cyclohexane, M.P.8.6 ℃, C.P51.4 ℃.
6) anti-, anti--4-oxyethyl group-4 '-the amyl group bis cyclohexane, M.P.35.2 ℃, C.P62.5 ℃.
7) anti-, anti--4-propoxy--4 '-the propyl group bis cyclohexane, M.P.14.5 ℃, C.P62.4 ℃.
Claims (9)
1. one kind prepares trans more than 90% of purity, the method of trans-4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound, it is characterized in that the trans-4-alkyl-cyclohexyl cyclohexyl ketone is dissolved in the organic solvent A, borane reducing agent hydride dissolves in the organic solvent B, two kinds of mixing solutionss of gained are mixed, carry out reduction reaction, adopt again Lewis acid to carry out translocation reaction, then carry out acidic hydrolysis, extract with solvent again, merge organic phase, be washed to neutrality, products therefrom is added siccative carry out drying, the filtering siccative is under the rough vacuum, remove solvent, can obtain a high proportion of trans, trans-4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound.
According to preparation purity claimed in claim 1 more than 90% trans, trans-method of 4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound, it is characterized in that with organic solvent prepared product being carried out recrystallization, make highly purified trans, trans-4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound.
According to preparation purity claimed in claim 1 more than 90% trans, trans-method of 4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound, it is characterized in that described organic solvent A, B all adopt at least a in the following material: ethanol, methyl alcohol, Virahol, 1,4-diox, tetrahydrofuran (THF), methyltetrahydrofuran, acetone, butanone; Described hydroborate adopts sodium borohydride or POTASSIUM BOROHYDRIDE.
According to preparation purity claimed in claim 1 more than 90% trans, trans-method of 4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound, it is characterized in that the used solvent of described extraction process adopts at least a in the lower material: toluene, ethyl acetate, methylene dichloride.
According to preparation purity claimed in claim 1 more than 90% trans, trans-method of 4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound, it is characterized in that the trans-4-alkyl-cyclohexyl cyclohexyl ketone for 1mol, employed borane reducing agent hydride is 0.1mol to 1.5mol, employed organic solvent A is 300-700ml, employed organic solvent B is 400-1000ml, and employed Lewis acid is 0.1-2.0mol.
According to preparation purity claimed in claim 1 more than 90% trans, trans-method of 4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound, it is characterized in that the temperature of reaction in the preparation process is-10 ℃ to 80 ℃.
According to preparation purity claimed in claim 6 more than 90% trans, trans-method of 4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound, it is characterized in that under 0 ℃ to 40 ℃, carrying out reduction reaction and Lewis acid translocation reaction, then, under 0 ℃ to 10 ℃, carry out acidic hydrolysis again.
According to preparation purity claimed in claim 2 more than 90% trans, trans-method of 4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound, it is characterized in that the used organic solvent of recrystallization is at least a in ethanol, methyl alcohol, Virahol, acetone, butanone, ethyl acetate, toluene, the methylene dichloride.
According to preparation purity claimed in claim 2 more than 90% trans, trans-method of 4-(4 '-alkyl-cyclohexyl) cyclohexyl alcohols liquid crystal intermediates compound, it is characterized in that the product for 1 times, carrying out the employed organic solvent of recrystallization is 0.5 to 5.0 times.
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| CN101337870A (en) * | 2008-08-08 | 2009-01-07 | 西安瑞联近代电子材料有限责任公司 | Method for synthesizing 4-(4'-n-alkyl cyclohexyl)cyclohexanone |
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Non-Patent Citations (2)
| Title |
|---|
| 杨永忠等.4-（4"-丙基环己基）环己醇的合成.《合成化学》.2004,第12卷(第6期),608-610. * |
| 蒋达荣.关于氢化铝锂和硼氢化钠还原醛酮成醇的反应式.《大学化学》.1997,第12卷(第4期),53-54. * |
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