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Preparation method of dimethyl L-dibenzoyl tartarate

A technology of benzoyl dimethyl tartrate and benzoyl tartaric acid is applied in the field of preparation of L-dibenzoyl tartrate, and can solve the problems that by-products and products are not easily separated, the yield of target products is low, and the variety of raw materials There are many problems such as avoiding the production of by-product benzoic acid, the color of the product is pure white, and the conversion rate is improved.

Active Publication Date: 2019-03-01
濮阳天健生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is in order to solve the L-dibenzoyl dimethyl tartrate preparation in the prior art to use raw material variety, the price is high, and the target product yield is low, by-product and product are not easy to separate in the preparation process, and product purity is low problem, and a kind of preparation method of L-dibenzoyl tartaric acid dimethyl ester proposed

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A kind of preparation method of L-dibenzoyl tartrate dimethyl that the present invention proposes comprises the following steps:

[0026] Preparation of S1, L-dibenzoyl tartaric anhydride:

[0027] a. Add toluene, L-tartaric acid and Lewis acid into the reaction kettle, heat up to 85°C while stirring, cool down to 75°C after stirring and mixing evenly, and then slowly add benzoyl chloride and thionyl chloride dropwise, controlled at 4h After the internal addition is completed, keep warm for 2 hours, follow the reaction by TLC, cool down to 30°C after the reaction is completed, and centrifuge to obtain the crude product of L-dibenzoyl tartaric anhydride, wherein the Lewis acid is ferric chloride, L-tartaric acid, benzoyl tartaric anhydride The mol ratio of acid chloride and thionyl chloride is 1:2:1.1; the mass ratio of L-tartaric acid and toluene is 1:1.6; the mass ratio of L-tartaric acid and Lewis acid is 1:0.0008;

[0028] b. Put the crude product of L-dibenzoyl tar...

Embodiment 2

[0035] A kind of preparation method of L-dibenzoyl tartrate dimethyl that the present invention proposes comprises the following steps:

[0036] Preparation of S1, L-dibenzoyl tartaric anhydride:

[0037] a. Add toluene, L-tartaric acid and Lewis acid into the reaction kettle, heat up to 88°C while stirring, cool down to 78°C after stirring and mixing evenly, and then slowly add benzoyl chloride and thionyl chloride dropwise, controlled at 4h The internal addition was completed, and the temperature was kept for 2 hours. TLC followed the reaction. After the reaction was completed, the temperature was lowered to 33°C, and the crude product of L-dibenzoyl tartaric anhydride was obtained by centrifugal separation. Among them, the Lewis acid was aluminum trichloride, L-tartaric acid, benzoyl The mol ratio of acid chloride and thionyl chloride is 1:2.02:1.1; the mass ratio of L-tartaric acid and toluene is 1:1.8; the mass ratio of L-tartaric acid and Lewis acid is 1:0.0009;

[0038...

Embodiment 3

[0045] A kind of preparation method of L-dibenzoyl tartrate dimethyl that the present invention proposes comprises the following steps:

[0046] Preparation of S1, L-dibenzoyl tartaric anhydride:

[0047] a. Add toluene, L-tartaric acid and Lewis acid into the reaction kettle, heat up to 90°C while stirring, cool down to 80°C after stirring and mixing evenly, and then slowly add benzoyl chloride and thionyl chloride dropwise, controlled at 4h After the internal addition was completed, the temperature was kept for 2 hours, and the reaction was tracked by TLC. After the reaction was completed, the temperature was lowered to 35°C, and the crude product of L-dibenzoyl tartaric anhydride was obtained by centrifugal separation. Among them, the Lewis acid was zinc chloride, L-tartaric acid, and benzoyl chloride The mol ratio with thionyl chloride is 1:2.05:1.1; The mass ratio of L-tartaric acid and toluene is 1:2; The mass ratio of L-tartaric acid and Lewis acid is 1:0.001;

[0048]...

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Abstract

The invention belongs to the technical field of a chemical synthesis method, and particularly relates to a preparation method of dimethyl L-dibenzoyl tartarate. The preparation method of the dimethylL-dibenzoyl tartarate comprises the following steps: S1, by taking L-tartaric acid, benzoyl chloride and thionyl chloride as raw materials, lewis acid as a catalyst and and toluene as a solvent, carrying out esterification and anhydridisation reaction, and purifying, thus obtaining an L-dibenzoyl tartaric acid anhydride wet product; S2, hydrolyzing the L-dibenzoyl tartaric acid anhydride wet product in pure water, thus obtaining an L-dibenzoyl tartaric acid hydrate wet product; S3, carrying out esterification reaction on the L-dibenzoyl tartaric acid hydrate wet product under the action of methanol and the catalyst, and purifying, thus obtaining the dimethyl L-dibenzoyl tartarate. According to the preparation method disclosed by the invention, raw materials are simple and easy to obtain, the reaction conditions are gentle, recycled methanol can be reused, the aftertreatment is convenient, and the preparation method is suitable for industrial production and is beneficial for being popularized.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis methods, in particular to a preparation method of L-dimethyl dibenzoyl tartrate. Background technique [0002] Dimethyl L-dibenzoyl tartrate can be used as an extraction selective agent for chiral drugs, as a chiral auxiliary for the synthesis of certain chiral drugs, as an auxiliary material for olefin polymerization catalysts, etc. [0003] In the prior art, the method for preparing L-dimethyl dibenzoyl tartrate is: react with dimethyl tartrate and benzoyl chloride, use many kinds of raw materials, the price is high, and the target product yield is low (≤75%) , is restricted on large-scale synthesis, and by product methyl benzoate is difficult for separating with product, and product purity is low (98.5%), and finished product yield is low (72.5%). Based on above statement, the present invention proposes a kind of preparation method of L-dibenzoyl tartaric acid dimethyl ester. Cont...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/78
CPCC07B2200/07C07C67/08C07C67/29C07D307/56C07C69/78
Inventor 李文廷袁国龙苏庆丰虎华张海清杨玉峰李志军楚静波毕庆伟苏熙盛张力天
Owner 濮阳天健生物科技有限公司
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