Synthesis of R-1-(3, 4-dimethylphenyl) ethanol and ester thereof

A technology of dimethyl phenyl and ethanol ester is applied in the field of preparation of optically pure chiral alcohols and esters, and achieves the effects of high application value, high selectivity and overcoming low product yield

Inactive Publication Date: 2015-01-28
王同俊
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the process of splitting and preparing R-1-(3,4-dimethylphenyl)ethanol ester, acidic resin is used as racemization catalyst, which not only overcomes the problem of low product yield, but also ensures the cheapness and ease of the catalyst. obtained, reusable and easy to realize industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0009] 1) Preparation of acyl donor p-chlorophenol ester

[0010] Add 500ml of dichloromethane to a 1000ml round bottom flask. Then add 128g (1mol) of p-chlorophenol, 72g (1.2mol) of acetic acid, 247.5g (1.2mol) of DCC, and 2.44g (0.02mol) of DMAP. Stir at room temperature for 10 hours, and detect the disappearance of p-chlorophenol by pointing the plate, then the reaction ends. The solution was filtered, concentrated, and then passed through the column to obtain 162.5 g of pure p-chlorophenol acetate, with a yield of 95.6%.

[0011] Other p-chlorophenol propionate, p-chlorophenol n-butyrate, p-chlorophenol n-valerate etc. can also be prepared according to this example.

[0012] 2) Preparation of R-1-(3,4-dimethylphenyl)ethanol ester by dynamic kinetic resolution

[0013] Add 250ml toluene to a 500ml conical flask, then add 68g (0.5mol) 1-(3,4-dimethylphenyl) ethanol, 93.5g (1.1mol) p-chlorophenol acetate, 3g CRL, 6g Acid resin CD550. After the addition, the Erlenmeyer fl...

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Abstract

The invention relates to a synthesis method of R-1-(3, 4-dimethylphenyl) ethanol and ester thereof. According to the synthesis method, 1-(3, 4-dimethylphenyl) ethanol is used as a raw material, lipase is used as a biological resolution catalyst, acidic resin is used as a recemization catalyst and p-chlorophenol is used as an acyl donor, R-1-(3, 4-dimethylphenyl) ethanol ester is obtained by dynamic kinetic resolution, and R-1-(3, 4-dimethylphenyl) ethanol is obtained through hydrolysis by LiOH. The synthesis method has the advantages that the synthesis method is mild in reaction and environment-friendly, and R-1-(3, 4-dimethylphenyl) ethanol is good in yield and high in selectivity, the used recemization catalyst is low in price and easily available, and the like, so that the synthesis method has an extremely high application value in the industrial production.

Description

technical field [0001] The invention relates to a method for preparing optically pure chiral alcohols and esters, in particular to a method for preparing dynamic kinetic resolution of R-1-(3,4-dimethylphenyl)ethanol and esters thereof. Background technique [0002] Chiral drugs are of great significance in the prevention and treatment of many diseases. Since the "reactantrin incident" in the pharmaceutical industry, the research on the synthesis of chiral drugs in human medicine, pesticides, and veterinary drugs has been paid more and more attention by governments and enterprises. Chiral alcohols and chiral esters are one of the important classes of chiral compounds, which can be used as important chiral intermediates and raw materials in the synthesis of pharmaceuticals and fine chemicals. [0003] The currently reported R-1-(3,4-dimethylphenyl)ethanol and its esters are mainly obtained by biological resolution of racemic alcohols, which can be further divided into kinetic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/20C07C29/09C07C69/157C07C67/03
CPCC07C67/08C07B2200/07C07C29/095C12P7/62C12P41/004C07C69/63C07C33/20
Inventor 王同俊
Owner 王同俊
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