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A kind of preparation method and its intermediate of 2-alkanoylmethyl-1,4-butanedioic acid derivative

A technology of alkanoylmethyl and succinic acid, which is applied in the field of preparation of 2-alkanoylmethyl-1,4-butanedioic acid derivatives, can solve problems such as safety risks, and achieve short reaction time and high reaction selection Good sex and less by-products

Active Publication Date: 2017-01-11
MAX RUDONG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such harsh reaction conditions require strict equipment, and high temperature and high pressure pose safety risks in industrial production

Method used

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  • A kind of preparation method and its intermediate of 2-alkanoylmethyl-1,4-butanedioic acid derivative
  • A kind of preparation method and its intermediate of 2-alkanoylmethyl-1,4-butanedioic acid derivative
  • A kind of preparation method and its intermediate of 2-alkanoylmethyl-1,4-butanedioic acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Preparation of 2-acetylmethyl-1,4-diethyl succinate

[0026] Step 1 Add 200 g of tert-butyl acetoacetate and 320 g of diethyl maleate to a 1 L three-neck equipped with a mechanical stirrer, a thermometer and a drying tube. 1.42 g of potassium tert-butoxide was added with stirring. After the addition, continue stirring for 5 h, add 400 mL of chloroform, 100 g of water and 7.06 g of industrial hydrochloric acid, and separate the organic phase. After precipitation of the organic phase, 410 g of diethyl 2-[(acetyl)(tert-butoxycarbonyl)]methyl-1,4-butanedioate was obtained. MS: m / z=330.1 ([M] + ).

[0027] Step 2 Add 408 g of diethyl 2-[(acetyl)(tert-butoxycarbonyl)]methyl-1,4-butanedioate, 1000 mL of toluene, and 21.6 g of p-toluenesulfonic acid into the reaction flask, and react for 2 h. After washing successively with 200 mL of water and 200 mL of 5% sodium bicarbonate solution, the solution was desolvated under reduced pressure to obtain 256 g of diethyl 2...

Embodiment 2

[0028] Example 2: Preparation of 2-benzoylmethyl-1,4-diethyl succinate

[0029] Step 1 Add 277 g of tert-butyl benzoylacetate and 320 g of diethyl maleate to a 1 L three-neck equipped with a mechanical stirrer, a thermometer and a drying tube. 14 g of potassium tert-butoxide was added with stirring. After the addition is complete, continue stirring for 4 h, add 400 mL of chloroform, 100 g of water and 7.06 g of industrial hydrochloric acid, and separate the organic phase. After precipitation of the organic phase, 490 g of diethyl 2-[(benzoyl)(tert-butoxycarbonyl)]methyl-1,4-butanedioate was obtained.

[0030] Step 2 Add 488 g of diethyl 2-[(acetyl)(tert-butoxycarbonyl)]methyl-1,4-butanedioate, 1,000 mL of toluene, and 21.6 g of p-toluenesulfonic acid into the reaction flask, and react for 3 hours. After washing successively with 200 mL of water and 200 mL of 5% sodium bicarbonate solution, the solution was desolvated under reduced pressure to obtain 300 g of diethyl 2-benzoy...

Embodiment 3

[0031] Example 3: Preparation of N-ethyl-2-acetylmethyl-1,4-succinimide

[0032] Step 1 Add 158 g of tert-butyl acetoacetate, 125 g of N-ethylmaleimide, and 500 mL of ethanol into a 1 L three-neck equipped with a mechanical stirrer, a thermometer and a drying tube. 7.8 g of sodium ethoxide was added with stirring. After the addition, the stirring reaction was continued for 8h. After desolvation under reduced pressure, 200 mL of chloroform, 100 g of water and 11.8 g of industrial hydrochloric acid were added to separate the organic phase, and the product after the desolvation of the organic phase was directly put into the next step.

[0033] Step 2: Add the product obtained in Step 1 into the reaction flask, add 600 mL of n-hexane and 13.7 g of p-toluenesulfonic acid, and react for 3 hours. Cool down, wash with 200mL of water and 150mL of 5% sodium bicarbonate solution successively, and precipitate under reduced pressure to obtain 165g of the product with a yield of 84%. MS:...

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Abstract

The invention discloses a preparation method and an intermediate of a 2-alkylacylmethyl-1,4-succinic acid derivative. The preparation method comprises the following steps of (1) reacting 2-alkylacyl tert-butyl acetate (I) and a compound (II) under the catalysis of alkali and under the condition that a solvent or no solvents are provided to obtain an intermediate (III); and (2) reacting the intermediate (III) under the catalysis of acid to obtain the 2-alkylacylmethyl-1,4-succinic acid derivative (IV). The preparation method is good in reaction selectivity and low in byproduct content; the process is simple, the reaction conditions are mild, and the reaction time is relatively short; and high-temperature and high-pressure reaction is avoided, requirements for equipment are not high, and the preparation method is safe in operation.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a preparation method of 2-alkanoylmethyl-1,4-butanedioic acid derivatives and an intermediate thereof. Background technique [0002] 2-Alkanoylmethyl-1,4-butanedioic acid derivatives are important organic intermediates widely used in the fields of medicine and pesticides. For example, 2-acetylmethyl-1,4-diethyl succinate is an important intermediate for the preparation of plant growth regulators trinexapac-ethyl and prohexadione (calcium) (CN102101830A and EP123001B1). Its structural formula is as shown in formula (V): [0003] [0004] There are many published patents about the synthesis technology of 2-acetylmethyl-1,4-diethyl succinate. For example, JP591663346, CN1850776A, CN102911058A, CN102101830A, CN104140368A and CN100588642C disclose a method for preparing compound (V) by addition of diethyl maleate and acetone as raw materials under the catalysis of diet...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/716C07C67/313
CPCC07C67/313C07C67/347C07C69/716
Inventor 盛秋菊刘伟平苏叶华陈玲张盼蔡国平虞小华陈邦池
Owner MAX RUDONG CHEM
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