Synthetic method for trans-4'-(4-alkylphenyl)(1,1'-bicyclohexane)-4-one

A technology of bicyclohexane and alkyl phenyl, which is applied in the field of liquid crystal intermediate synthesis, can solve the problems of cumbersome post-processing, many reaction steps, long time consumption, etc., and achieves the effects of saving water washing operation, simplifying operation and low overall cost

Pending Publication Date: 2020-02-14
XIAN RUILIAN NEW MATERIAL CO LTD
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In order to overcome the above-mentioned shortcomings of many reaction steps, cumbersome post-treatment, long time-consuming, and a lot of waste water, the present invention provides a trans-4'-(4-alkylphenyl)(1,1'-bicyclohexane)-4 -The synthesis method of ketone has the advantages of shortening process steps, simplifying post-treatment operations, reducing process time consumption, and reducing waste water volume, which is suitable for large-scale industrial production

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  • Synthetic method for trans-4'-(4-alkylphenyl)(1,1'-bicyclohexane)-4-one
  • Synthetic method for trans-4'-(4-alkylphenyl)(1,1'-bicyclohexane)-4-one

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preparation example Construction

[0041] The invention provides a synthetic method of trans-4'-(4-alkylphenyl)(1,1'-bicyclohexyl)-4-one, comprising the following steps:

[0042] S1: Grignard reaction between 4-alkyl halobenzene and magnesium powder, followed by adding dicyclohexanone ethylene glycol monoketal to generate a mixture containing the compound of formula (II), the reaction equation is as follows:

[0043]

[0044] S2: add acid to the mixture containing the compound of formula (II) in S1 to carry out dehydration and deprotection reaction to generate the compound of formula (III), the reaction equation is as follows:

[0045]

[0046] The mol ratio of described acid and dicyclohexanone ethylene glycol monoketal is 5-15:1, and described acid is hydrochloric acid, sulfuric acid, formic acid or acetic acid;

[0047] S3: The compound of formula (Ⅲ) is hydrogenated under the action of a catalyst to generate the compound of formula (Ⅳ), and the reaction equation is as follows:

[0048]

[0049] S4...

Embodiment 1

[0053] (1) Preparation of a mixture containing a compound of formula (II)

[0054] Under the protection of nitrogen, sequentially add 200ml of tetrahydrofuran and 152.6g of magnesium powder into a dry 10L three-necked flask, and start stirring. The system is heated to 57°C, 0.07g of iodine is added, and 19.4g of 4-methylchlorobenzene is added dropwise to trigger Grignard After the initiation is successful, add 390g of methyl chlorobenzene diluted with 823ml of tetrahydrofuran dropwise. During the dropping process, the temperature is controlled at 70°C. Hexanone ethylene glycol monoketal and 5060ml of toluene solution, the dropwise addition is completed, after 1 hour of heat preservation at 60°C, the reaction is stopped, and the reaction solution is directly used for the next step reaction, GC>95.0%, the yield of this step is calculated as 100% ;

[0055] (2) Preparation of intermediate formula (Ⅲ) compound

[0056] Under the protection of nitrogen, add 1484g of 70% sulfuric ...

Embodiment 2

[0062] (1) Preparation of a mixture containing a compound of formula (II)

[0063] Under the protection of nitrogen, sequentially add 240ml of tetrahydrofuran and 68.7g of magnesium powder into a dry 10L three-necked flask, and start stirring. The system is heated to 55°C, 0.07g of iodine is added, and 41.5g of 4-methylchlorobenzene is added dropwise to trigger a Grignard reaction. , after successful initiation, add dropwise 200g of methyl chlorobenzene diluted with 2174ml of tetrahydrofuran, and control the temperature at 60°C for weak reflux during the dropping process. The tetrahydrofuran solution, after the dropwise addition is completed, if the reaction is refluxed at 70°C for 1 hour, the reaction is stopped, and the reaction solution is directly used for the next step reaction, GC>98.0%, and the yield of this step is calculated as 100%;

[0064] (2) Preparation of intermediate formula (Ⅲ) compound

[0065] Under the protection of nitrogen, add 1934.5g of 30% hydrochlori...

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Abstract

The invention discloses a synthetic method for trans-4'-(4-alkylphenyl)(1,1'-bicyclohexane)-4-one, and belongs to the technical field of synthetic methods of liquid crystal intermediates. The method includes the following steps: by using p-alkyl halogenated benzene as a starting material, performing grignard coupling, performing dehydration deprotection, performing hydrogenation, and performing transformation to obtain the trans-4'-(4-alkylphenyl)(1,1'-bicyclohexane)-4-one. The preparation method of the compound provided by the invention is a simple and has mild reaction conditions, combinestraditional two-step reactions of dehydration and deprotection into one step, and achieves the purpose of shortening the route, simplifying the post-treatment, and saving the time cost; and the methodhas the advantages of combining the reaction steps, shortening the route, simplifying the operation and reducing the wastewater amount, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of liquid crystal intermediate synthesis methods, and in particular relates to a synthesis method of trans-4'-(4-alkylphenyl)(1,1'-bicyclohexyl)-4-one. Background technique [0002] trans-4'-(4-alkylphenyl)(1,1'-bicyclohexyl)-4-one as liquid crystal monomer 1-[(trans,trans)-4-(3-butene -1-yl)[1,1-bicyclohexyl]-4-yl]-4-alkyl-benzene is an indispensable intermediate, and the patent JP2014162752 adopts the following synthetic route: [0003] [0004] The synthesis route has many reaction steps, long synthesis route, cumbersome post-treatment, and long overall process time, resulting in high time cost; the four-step water washing process except the hydrogenation step results in a large amount of process wastewater. In today's increasingly severe environmental protection situation, It is very unsuitable for mass production. Contents of the invention [0005] In order to overcome the above-mentioned shortco...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/67C07C45/62C07C49/657C07F3/02C07D317/72C07C45/51C07C49/683
CPCC07C45/67C07C45/62C07F3/02C07D317/72C07C45/515C07C2601/14C07C2601/16C07B2200/07C07C49/683C07C49/657Y02P20/55
Inventor 巨妮娟段迎春蔡文刚张鸿宝高仁孝
Owner XIAN RUILIAN NEW MATERIAL CO LTD
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