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Preparation method of p-chlorine methyl cinnamate

A technology of methyl cinnamate and methyl acetate, applied in the field of preparation of methyl p-chlorocinnamate, can solve the problems of not meeting green production requirements, many side reactions, poor production conditions, etc., and achieves stable and reliable product quality, recycling The effect of convenient circulation and mild reaction conditions

Inactive Publication Date: 2012-09-12
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 to a three-necked flask, and 7.4g (0.0525mol) p-chlorobenzaldehyde was added in 8 batches within 1.0h under stirring to keep the temperature at Below 5°C, after the addition is completed, let it react at room temperature for 2 hours, slowly add 5% by mass sulfuric acid dropwise to adjust the pH of the reaction solution between 6.5 and 7.2; filter, the filtrate obtained is the ionic liquid and the phase transfer catalyst TBAB The mixed solution is distilled under reduced pressure to remove water and saturated Na 2 CO 3 After the treatment, the solid is recycled and used, and the obtained solid is washed with hot water at 50-60°C, washed with 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 to a three-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, let it react at room temperature for 3 hours, slowly add 5% by mass sulfuric acid dropwise to adjust the pH of the reaction solution between 6.5 and 7.2; filter, the filtrate obtained is a mixture of ionic liquid and phase transfer catalyst TBAB Liquid, remove water and saturated Na by distillation under reduced pressure 2 CO 3 After treatment, the solid is recycled and used, and the obtained solid is washed with hot water at 50-60°C, washed with 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 to a three-necked flask, and 25.3g (0.18mol) p-chlorobenzaldehyde was added in 9 batches under stirring within 1.5h to keep the temperature at 5 Below ℃, after the addition, let it react at room temperature for 3.5h, slowly add 5% by mass sulfuric acid dropwise to adjust the pH of the reaction solution between 6.5 and 7.2; filter, the filtrate obtained is the ionic liquid and the phase transfer catalyst TBAB The mixed solution is distilled under reduced pressure to remove water and saturated Na 2 CO 3 After treatment, the solid is recycled and used, and the obtained solid is washed with hot water at 50-60°C, washed with 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 organic synthesis intermediates, in particular to a preparation method of methyl p-chlorocinnamate. Background technique [0002] Methyl p-chlorocinnamate, also known as methyl 4-chlorocinnamate, is used as an organic synthesis intermediate, mainly used in the fields of medicine, fine chemicals, and material chemicals. [0003] Cinnamate is mainly obtained by Claisen-Schmidt condensation reaction of benzaldehyde and acetate. The main methods for preparing cinnamate by Claisen-Schmidt reaction are as follows: 1. Use absolute ethanol as solvent and 10% by mass NaOH as catalyst. However, this method has a long reaction time, many side reactions, and low product yield. The benefit is poor. 2. Condensed with acetate as solvent and sodium alkoxide as catalyst. This method improves the product yield, but the post-processing is complicated and the purification is difficult. In the above preparation methods, all raw ...

Claims

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Application Information

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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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