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Synthesis of R-1-(2,3-dimethyl phenyl) ethyl alcohol and ester thereof

A technology of dimethylphenyl and ethanol ester is applied in the field of preparation of optically pure chiral alcohols and esters to achieve the effects of good product yield, mild conditions and environmental friendliness

Inactive Publication Date: 2015-02-11
王同俊
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the process of splitting and preparing R-1-(2,3-dimethylphenyl)ethanol ester, acidic resin is used as racemization catalyst, which not only overcomes the problem of low product yield, but also ensures that the catalyst is cheap and easy. 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 n-valeric 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-(2,3-dimethylphenyl)ethanol ester by dynamic kinetic resolution

[0013] Add 250ml toluene to a 500ml conical flask, then add 68g (0.5mol) 1-(2,3-dimethylphenyl) ethanol, 93.5g (1.1mol) p-chlorophenol acetate, 3g CRL, 6g Acid resin CD550. After the addition, the Erlenmeyer...

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Abstract

The invention relates to a synthesis method of R-1-(2,3-dimethyl phenyl) ethyl alcohol and an ester thereof. The method comprises the following steps: carrying out dynamic kinetic resolution on a chlorophenol ester taken as an acyl donor by taking 1-(2,3-dimethyl phenyl) ethyl alcohol as a raw material, lipase as a biological resolution catalyst and acidic resins as an racemase catalyst so as to obtain a R-1-(2,3-dimethyl phenyl) ethyl alcohol ester; and then hydrolyzing the R-1-(2,3-dimethyl phenyl) ethyl alcohol ester with LiOH so as to obtain the R-1-(2,3-dimethyl phenyl) ethyl alcohol. The method has the advantages of mild condition, environmental friendliness, good yield and high selectivity of the R-1-(2,3-dimethyl phenyl) ethyl alcohol and the like; and the adopted racemase catalyst is low in price and is easily available. Thus, the method provided by the invention has an ultrahigh application value in 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 dynamic resolution of R-1-(2,3-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-(2,3-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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IPC IPC(8): C12P41/00C12P7/22C12P7/62
Inventor 王同俊
Owner 王同俊