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Preparation method of p-chlorine methyl cinnamate

A technology of methyl cinnamate and methyl acetate, which is applied in the field of preparation of methyl p-chlorocinnamate, can solve problems such as non-compliance with green production requirements, poor production conditions, and many side reactions, and achieve stable and reliable product quality and responsiveness. The effect of mild conditions and convenient recycling

Inactive Publication Date: 2014-04-02
湖北远成赛创科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method that prepares cinnamate with Claisen-Schmidt reaction mainly contains: 1, take dehydrated alcohol as solvent, and mass percent 10%NaOH is prepared as catalyzer, but this method reaction time is long, and side reaction is many, and product yield is low, and production Poor benefit
2. It is formed by condensation with acetate as solvent and sodium alkoxide as catalyst. This method improves the product yield, but the post-treatment is complicated and the purification is difficult.
Due to the many steps of this process, poor production conditions, low product yield, high cost and serious pollution, it does not meet the requirements of green production

Method used

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  • Preparation method of p-chlorine methyl cinnamate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 0.06mol ionic liquid [bmim] 2 CO 3 , 0.2g (0.0006mol) TBAB and 3.7g (0.05mol) methyl acetate were added in the there-necked flask, and 7.4g (0.0525mol) p-chlorobenzaldehyde was added in 8 batches within 1.0h under stirring, keeping the temperature at Below 5°C, after adding, let it react at room temperature for 2 hours, slowly add 5% sulfuric acid by mass percentage dropwise, so that the pH of the reaction solution is regulated between 6.5 and 7.2; filter, and the obtained filtrate is the mixture of ionic liquid and phase transfer catalyst TBAB The mixture was distilled under reduced pressure to remove water, saturated Na 2 CO 3 After treatment, the obtained solid was washed with hot water at 50-60° C., ice water, and dried to obtain 8.7 g of methyl p-chlorocinnamate with a purity of 98.8% and a yield of 87.4% (calculated as methyl acetate).

Embodiment 2

[0028] 0.14mol ionic liquid [bmim] 2 CO 3 , 0.6g (0.002mol) TBAB and 7.4g (0.1mol) methyl acetate were added in the there-necked flask, and 15.5g (0.11mol) p-chlorobenzaldehyde was added in 8 batches within 1.0h under stirring to keep the temperature at 5 Below ℃, after the addition is completed, let it react at room temperature for 3 hours, slowly add 5% sulfuric acid by mass percentage dropwise, so that the pH of the reaction solution is controlled between 6.5 and 7.2; filter, and the obtained filtrate is a mixture of ionic liquid and phase transfer catalyst TBAB liquid, distilled under reduced pressure to remove water, saturated Na 2 CO 3 After treatment, the obtained solid was washed with hot water at 50-60° C., ice water, and dried to obtain 17.5 g of methyl p-chlorocinnamate with a purity of 99.1% and a yield of 88.2% (calculated as methyl acetate).

Embodiment 3

[0030] 0.24mol ionic liquid [bmim] 2 CO 3 , 1.5g (0.0046mol) TBAB and 11.1g (0.15mol) methyl acetate were added in the there-necked flask, and 25.3g (0.18mol) p-chlorobenzaldehyde was added in 9 batches within 1.5h under stirring to keep the temperature at 5 Below ℃, after adding, make it react at room temperature for 3.5 hours, slowly add 5% sulfuric acid by mass percentage dropwise, so that the pH of the reaction solution is regulated between 6.5 and 7.2; filter, and the obtained filtrate is the mixture of ionic liquid and phase transfer catalyst TBAB The mixture was distilled under reduced pressure to remove water, saturated Na 2 CO 3 After treatment, the obtained solid was washed with hot water at 50-60° C., ice water, and dried to obtain 27.3 g of methyl p-chlorocinnamate with a purity of 99.4% and a yield of 92.0% (calculated as methyl acetate).

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Abstract

The invention provides a preparation method of p-chlorine methyl cinnamate, which comprises the following steps: taking basic ionic liquid 1-butyl-3-methylimidazole carbonate as a solvent and a catalyst, tetrabutyl ammonium bromide as a phase-transfer catalyst for stirring and mixing with methyl acetate under the temperature of 5 DGE C, then adding p-chlorine benzaldehyde for a condensation reaction, adding dilute sulfuric acid after the reaction, wherein the pH value of a reaction solution is between 6.5 and 7.2; filtering, wherein the obtained filtrate can be taken as a mixed liquid of ionic liquid and the phase-transfer catalyst; filtering the obtained solid, washing and drying to obtain p-chlorine methyl cinnamate. The method of the invention has the advantages of simple method, mild reaction condition, convenient operation, easy catalyst recovery and multitime repetitive usage; the product has the advantages of reliable and stable quality, high yield and no environmental pollution, and the method of the invention is a green synthetic method.

Description

technical field [0001] The invention relates to a preparation method of an organic synthesis intermediate, in particular to a preparation method of methyl p-chlorocinnamate. Background technique [0002] Methyl p-chlorocinnamate, also known as methyl 4-chlorocinnamate, as an organic synthesis intermediate, is mainly used in the fields of medicine, fine chemical industry, and material chemical industry. [0003] Cinnamate is mainly obtained by Claisen-Schmidt condensation reaction of benzaldehyde and acetate. The method that prepares cinnamate with Claisen-Schmidt reaction mainly contains: 1, take dehydrated alcohol as solvent, and mass percent 10%NaOH is prepared as catalyzer, but this method reaction time is long, and side reaction is many, and product yield is low, and production The benefits are poor. 2. It is formed by condensation with acetate as a solvent and sodium alkoxide as a catalyst. This method improves the product yield, but the post-treatment is complicated ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/343C07C69/65
CPCY02P20/584
Inventor 叶思朱如慧杨洁韩洪杰徐海林
Owner 湖北远成赛创科技有限公司
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