R-1-(3-methylphenyl)ethanol and synthesis of ester thereof

A technology of methyl phenyl and ethanol ester is applied in the field of preparation of optically pure chiral alcohols and esters to achieve the effects of overcoming low product yield, environmental friendliness and high selectivity

Inactive Publication Date: 2015-01-07
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-(3-methylphenyl)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 to obtain. Reusable, 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 156.9 g of pure p-chlorophenol acetate, with a yield of 92.3%.

[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-methylphenyl)ethanol ester by dynamic kinetic resolution

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

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PUM

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Abstract

The invention discloses R-1-(3-methylphenyl)ethanol and a synthetic method of an ester thereof. The preparation method of R-1-(3-methylphenyl)ethanol comprises the following steps: taking 1-(3-methylphenyl)ethanol as a raw material, lipase as a biologic resolution catalyst, acidic resin as a racemization catalyst, and p-chlorophenol ester as an acyl donor, conducting dynamic kinetic resolution to obtain R-1-(3-methylphenyl)ethanol ester, and then conducting LiOH hydrolysis to obtain R-1-(3-methylphenyl)ethanol. The R-1-(3-methylphenyl)ethanol and the synthetic method of the ester thereof disclosed by the invention have the advantages of mild conditions, environment friendliness, good product yield, high selectivity and cheap price and good feasibility of the adopted racemization catalyst, so that the technology has a high 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-(3-methylphenyl)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-methylphenyl)ethanol and its esters are mainly obtained by biological resolution of racemic alcohols, which can be further divided into kinetic resoluti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/92C07C33/20C12P41/00C12P7/22
CPCC07C67/08C07B2200/07C07C29/095C12P7/62C12P41/004C07C69/63C07C33/20
Inventor 王同俊
Owner 王同俊
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