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Synthesis method of (1R, 2R)-trans-cyclohexane dicarboxylic acid

A technology of cyclohexanedicarboxylic acid and synthesis method, which is applied in the field of compound synthesis, can solve the problems of long steps, low yield, and many waste liquids, and achieve high recovery rate, high crystallization efficiency, and high reaction conversion rate Effect

Inactive Publication Date: 2015-09-30
JINAN PANSHI PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to solve the problems in the above prior art of preparing (1R,2R)-trans cyclohexanedicarboxylic acid with relatively long steps, low yield and more waste liquid, the application provides a relatively simple operation Synthetic method of (1R,2R)-trans-cyclohexanedicarboxylic acid with high yield and virtually no waste liquid generation

Method used

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  • Synthesis method of (1R, 2R)-trans-cyclohexane dicarboxylic acid
  • Synthesis method of (1R, 2R)-trans-cyclohexane dicarboxylic acid
  • Synthesis method of (1R, 2R)-trans-cyclohexane dicarboxylic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Take 15g of cis-hexahydrophthalic anhydride and 150ml of 70% sulfuric acid solution in a reaction flask, heat to reflux at 120°C for 26 hours, neutralize with 10% sodium hydroxide, add activated carbon at the same time, stir for 1 hour, filter, and the filtrate is neutralized with hydrochloric acid To pH = 2, stirred for 1 h, filtered to obtain a white granular product of a mixture of cis-1,2-cyclohexanedicarboxylic acid and (1R,2R)-trans-cyclohexanedicarboxylic acid (15:85) 10.1g.

[0027] The mixture in the previous step was heated to reflux with 4 times of isopropyl ether for 1 hour, then lowered to room temperature, and solids were slowly precipitated during the cooling process, stirred at room temperature for 2 hours, filtered, and dried to obtain a crude product with higher purity, and then Then heated to reflux with 4 times of isopropyl ether to dissolve, lowered to room temperature, stirred for 2 hours, filtered, and dried to obtain 6.4 g of white particles (1R,...

Embodiment 2

[0029] Take 15g of cis-hexahydrophthalic anhydride and 300ml of 48% hydrobromic acid solution in a reaction flask, heat at 120°C for 18 hours, neutralize with 10% sodium hydroxide, add activated carbon at the same time, stir for 1 hour, filter, and the filtrate is neutralized with hydrochloric acid and to pH=2, stirred for 1h, filtered to obtain a mixture of white granular product cis-1,2-cyclohexanedicarboxylic acid and (1R,2R)-trans-cyclohexanedicarboxylic acid (HPLC, 14 :86) 11.0 g.

[0030] The mixture in the previous step was heated to reflux with 4 times of isopropyl ether for 1 hour, then lowered to room temperature, and solids were slowly precipitated during the cooling process, stirred at room temperature for 2 hours, filtered, and dried to obtain a crude product with higher purity, and then Then heated to reflux with 4 times isopropyl ether to dissolve, lowered to room temperature, stirred for 2 hours, filtered, and dried to obtain 7.2 g of (1R,2R)-trans-cyclohexaned...

Embodiment 3

[0032] Take 15g of cis-hexahydrophthalic anhydride and 300ml of 48% acetic acid solution in a reaction flask, heat at 120°C for 20 hours, neutralize with 10% sodium hydroxide, add activated carbon at the same time, stir for 1 hour, filter, and neutralize the filtrate with hydrochloric acid to pH=2, stirred for 1h, filtered to obtain a mixture of white granular product cis-1,2-cyclohexanedicarboxylic acid and (1R,2R)-trans-cyclohexanedicarboxylic acid (HPLC, 20:80 ) 11.2g.

[0033] The mixture in the previous step was heated to reflux with 4 times of isopropyl ether for 1 hour, then lowered to room temperature, and solids were slowly precipitated during the cooling process, stirred at room temperature for 2 hours, filtered, and dried to obtain a crude product with higher purity, and then Then heated to reflux with 4 times isopropyl ether to dissolve, lowered to room temperature, stirred for 2 hours, filtered, and dried to obtain 6.1 g of (1R,2R)-trans-cyclohexanedicarboxylic ac...

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Abstract

The invention relates to the technical field of compound synthesis and in particular relates to a synthesis method of a (1R, 2R)-trans-cyclohexane dicarboxylic acid. According to the synthesis method, cis-hexahydrobenzene anhydride is directly hydrolyzed in the presence of an acid catalyst to obtain the mixture of cis- and (1R, 2R)-trans-cyclohexane dicarboxylic acids; and then the mixture is recrystallized by use of a solvent to obtain relatively pure (1R, 2R)-trans-cyclohexane dicarboxylic acid. The method is relatively simple to operate; the cis-hexahydrobenzene anhydride is hydrolyzed by use of a mixed acid and the proportion of the (1R, 2R)-trans-cyclohexane dicarboxylic acid in the obtained mixture is high, and therefore, the reaction conversion rate is high and the cost is saved; as the mixed solvent is used for recrystallization, the recrystallization efficiency is high, the recovery rate is high, the cost is saved and the market competitiveness is increased; the high-purity and high-yield (1R, 2R)-trans-cyclohexane dicarboxylic acid is obtained, and the high-purity product can be obtained by virtue of once recrystallization; a little solvent is used and the solvent can be recycled.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to a method for synthesizing (1R, 2R)-trans cyclohexanedicarboxylic acid. Background technique [0002] The structure of (1R,2R)-trans-cyclohexanedicarboxylic acid is as follows: [0003] [0004] The preparation process in the prior art generally uses cis-hexahydrophthalic anhydride as a raw material, undergoes alkalinization and hydrolysis, and then performs isomerization with an acid as a catalyst, and selects a chiral reagent for resolution. The steps are long and the yield is not high. , and more waste liquid is generated, the route is as follows: [0005] Contents of the invention [0006] In order to solve the problems in the above prior art of preparing (1R,2R)-trans cyclohexanedicarboxylic acid with relatively long steps, low yield and more waste liquid, the application provides a relatively simple operation A method for synthesizing (1R,2R)-trans-cyclo...

Claims

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Application Information

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IPC IPC(8): C07C51/087C07C61/09
CPCC07C51/087C07C2601/14C07C61/09
Inventor 郝胜先桑运福楼志腾石清慧柳海杰
Owner JINAN PANSHI PHARMA TECH
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