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A kind of method for synthesizing methyl 3,4,5-trimethoxybenzoate by one-step method

A technology of methyl trimethoxybenzoate and dimethylformamide, which is applied in the chemical field, can solve the problems of incomplete reaction of raw materials, complicated and lengthy process, and high degree of danger, so as to save time and cost, simplify the preparation process, The effect of reducing pollution

Active Publication Date: 2018-03-30
JIURUI BIOLOGY & CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] There are still many deficiencies in the above two synthesis techniques: (1) two-step synthesis method: this method requires two-step synthesis, and each step needs to be purified and refined. The process is cumbersome and lengthy, time-consuming and labor-intensive, and reduces the yield; During the esterification reaction, the reaction is a reversible reaction, and the reaction of the raw materials is not complete, which reduces the yield and causes unnecessary waste; the dimethyl sulfate used in the reaction is a highly toxic chemical, and the degree of danger is high during production.
(2) One-step synthesis method: This method combines two steps into one step. Although the tedious process of intermediate purification and purification is saved, the highly toxic dimethyl sulfate is still used.

Method used

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  • A kind of method for synthesizing methyl 3,4,5-trimethoxybenzoate by one-step method
  • A kind of method for synthesizing methyl 3,4,5-trimethoxybenzoate by one-step method

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Effect test

Embodiment 1

[0026] Embodiment 1: the method for one-step synthetic 3,4,5-trimethoxymethylbenzoate, concrete method and step are:

[0027] (1) Add 20g of gallic acid, 500ml of DMF, and 20g of potassium carbonate into a four-necked bottle, stir and cool down to below 10°C, pass 50g of chloromethane gas, immediately raise the temperature from 40°C to 110°C within 12 hours , then down to room temperature, concentrated distillation;

[0028] (2) Add 300 mL of water to the concentrated solution, keep stirring, extract three times with ethyl acetate, combine the extracts, concentrate and distill the extracts to obtain a white solid, which is the crude product.

[0029] (3) Put the crude product into 100mL of methanol, stir and heat up to 60-65°C, reflux for 1 hour and then cool down to room temperature. After concentrated distillation, suction filtration and drying, 22.5g of pure product was obtained, the yield was 84.6%, the content was 99.61% by HPLC, and the melting point was 82°C~83°C.

Embodiment 2

[0030] Embodiment 2: the method for one-step synthetic 3,4,5-trimethoxymethylbenzoate, concrete method and step are:

[0031] (1) Add 40g of gallic acid, 1200mL of DMF, and 100g of potassium carbonate into a four-neck bottle, stir and cool down to below 10°C, pass 100g of chloromethane gas, and immediately raise the temperature from 40°C to 110°C within 10 hours , then down to room temperature, concentrated distillation;

[0032] (2) Add 600 mL of water to the concentrated solution, keep stirring, extract three times with ethyl acetate, combine the extracts, concentrate and distill the extracts to obtain a white solid, which is the crude product.

[0033] (3) Put the crude product into 200mL of methanol, stir and heat up to 60-65°C, reflux for 1 hour and then cool down to room temperature. After suction filtration and drying, 45.4g of pure product was obtained, the yield was 85.3%, the content was 99.57% by HPLC, and the melting point was 82°C~83°C.

Embodiment 3

[0034] Embodiment 3: the method for synthesizing 3,4,5-trimethoxymethylbenzoate in one step, concrete method and step are:

[0035] (1) Add 40g of gallic acid, 1500mL of DMF, and 120g of potassium carbonate into a four-neck bottle, stir and cool down to below 10°C, pass 100g of chloromethane gas, and immediately raise the temperature from 40°C to 110°C within 5 hours , then down to room temperature, concentrated distillation;

[0036] (2) Add 600 mL of water to the concentrated solution, keep stirring, extract three times with ethyl acetate, combine the extracts, concentrate and distill the extracts to obtain a white solid, which is the crude product.

[0037] (3) Put the crude product into 200mL of methanol, stir and heat up to 60-65°C, reflux for 1 hour and then cool down to room temperature. After concentrated distillation, suction filtration and drying, 44.8g of pure product was obtained, the yield was 84.2%, the content was 99.88% by HPLC, and the melting point was 83°C~...

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Abstract

The invention provides a method for synthesizing methyl 3,4,5-trimethoxybenzoate by using a one-step method. The method comprises the following steps: by taking gallic acid as a raw material, performing esterification reaction on N,N-dimethyl formamide as a solvent and a chloromethane gas, thereby preparing methyl 3,4,5-trimethoxybenzoate at one step. In the reaction process, potassium carbonate is taken as an acid-binding agent. The method is convenient and feasible, simple and convenient to operate, efficient and environmentally friendly, and applicable to commercial large-scale production, and ever-increasing market requirements can be met.

Description

technical field [0001] The invention relates to the technical field of chemistry, in particular to a method for synthesizing methyl 3,4,5-trimethoxybenzoate. technical background [0002] Methyl 3,4,5-trimethoxybenzoate, a white crystalline solid, is an important intermediate in organic synthesis. Starting from this substance, a variety of pharmaceutical products can be obtained, such as antibacterial synergistic drug trimethoprim, anxiolytic drug trimetazine, gastrointestinal drug trimebutine maleate, etc., and can also be used in heat-sensitive recording materials Used as a UV absorber. With the continuous development of the chemical industry, methyl 3,4,5-trimethoxybenzoate has a broader market prospect. Therefore, methyl 3,4,5-trimethoxybenzoate can be produced simply and efficiently There are great social benefits. [0003] At present, a two-step method is often used in the industry. The specific process is: use gallic acid as a raw material, perform a methylation re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/31C07C69/92
CPCC07C67/11C07C67/31C07C69/92
Inventor 杨彦明陈波王文龙赵国锋
Owner JIURUI BIOLOGY & CHEM CO LTD
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