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A kind of method for synthesizing methyl 3,4,5-trimethoxybenzoate from gallic acid

A technology for methyl trimethoxybenzoate and methyl gallate, which is applied in the field of preparing methyl 3,4,5-trimethoxybenzoate, can solve the problem of great harm to people and the environment, incomplete reaction of raw materials, and reduced Yield and other problems, to achieve the effect of less waste, improved product yield, and reduced production costs

Active Publication Date: 2018-04-06
JIURUI BIOLOGY & CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There are still many deficiencies in this existing technology: the dimethyl sulfate used in the reaction belongs to highly toxic chemicals, which is extremely harmful to people and the environment; during the second step esterification reaction, the reaction is a reversible reaction, and the raw material reaction is not complete. Reduce productivity and cause unnecessary waste

Method used

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  • A kind of method for synthesizing methyl 3,4,5-trimethoxybenzoate from gallic acid
  • A kind of method for synthesizing methyl 3,4,5-trimethoxybenzoate from gallic acid
  • A kind of method for synthesizing methyl 3,4,5-trimethoxybenzoate from gallic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: a kind of method that gallic acid synthesizes 3,4,5-trimethoxybenzoic acid methyl ester, concrete method and steps are as follows:

[0028] (1) Add 500g of gallic acid, 2000ml of methanol, and 25g of concentrated sulfuric acid into a four-neck flask, heat up and reflux for 2 hours, then cool down, concentrate, distill, and suction filter to obtain methyl gallate as a solid.

[0029] (2) Add 2500ml of toluene to methyl gallate for washing, and then filter with suction after about 1 hour to obtain about 500g of solid matter.

[0030] (3) Take another four-neck bottle, add 20g of methyl gallate obtained in step (2) (the methyl gallate used in the following examples are all prepared in Example 1.), DMF100ml, sodium hydroxide 6g, stir Cool down to below 10°C, pass through 40g of chloromethane gas, heat up to 30°C after passing through, keep warm for 3 hours, then cool down to room temperature, concentrate and distill;

[0031] (4) Add 200ml of water to the con...

Embodiment 2

[0033] Embodiment 2: a kind of method that gallic acid synthesizes 3,4,5-trimethoxybenzoic acid methyl ester, concrete method and steps are as follows:

[0034] (1) Add 40g of methyl gallate, 320ml of DMF, and 32g of sodium carbonate into a four-neck bottle, stir and cool down to below 10°C, pass 80g of methyl chloride gas, and heat up to 60°C after passing through, keep warm for 8 hours and then cool down to room temperature, concentrated distillation;

[0035] (2) Add 400ml of water to the concentrated solution, and keep stirring, filter with suction after about half an hour, and take the filter residue to obtain crude methyl 3,4,5-trimethoxybenzoate.

[0036] (3) Put the crude product into 400ml of methanol, stir and heat up to 60-65°C, reflux for 1 hour and then cool down to room temperature, concentrate and distill, filter with suction and dry to obtain 46.0g of pure product, the yield is 86.5%, and the content is determined by HPLC The detection rate is 99.0%, and the m...

Embodiment 3

[0037] Embodiment 3: a kind of method that gallic acid synthesizes 3,4,5-trimethoxybenzoic acid methyl ester, concrete method and steps are as follows:

[0038] (1) In a four-necked bottle, add 80g of methyl gallate, 480ml of DMF, and 24g of potassium carbonate, stir and lower the temperature to below 10°C, pass 160g of methyl chloride gas, and heat up to 55°C after passing through, keep warm for 8 hours and then cool down to room temperature, concentrated distillation;

[0039] (2) Add 800ml of water to the concentrated solution and keep stirring, filter with suction after about half an hour, and take the filter residue to obtain crude methyl 3,4,5-trimethoxybenzoate.

[0040] (3) Put the crude product into 800ml of methanol, stir and heat up to 60-65°C, reflux for 1 hour and then cool down to room temperature, concentrate and distill, filter with suction and dry to obtain 90.8g of pure product, the yield is 85.3%, the content is determined by HPLC The detection rate is 99.6...

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Abstract

The invention discloses a method for synthesizing methyl 3,4,5-trimethoxybenzoate from gallic acid. The method comprises the following steps: by using gallic acid as a raw material, carrying out esterification on the gallic acid and methanol under the catalytic action of sulfuric acid to generate methyl gallate, carrying out methylation reaction on the methyl gallate and methyl chloride gas at 20-60 DEG C, and preparing the methyl 3,4,5-trimethoxybenzoate by using N,N-dimethylformamide as a solvent and any one of sodium carbonate, sodium hydroxide, potassium carbonate, potassium hydroxide and inorganic alkaline compounds as an acid-binding agent. The method is convenient and feasible, is simple to operate, has the advantages of high efficiency and environmental protection, can be used for commercialized large-scale production, and satisfies the ever-growing market demands.

Description

Technical field: [0001] The invention belongs to the technical field of chemical industry, in particular to a method for preparing methyl 3,4,5-trimethoxybenzoate with gallic acid. technical background: [0002] 3,4,5-Methyl 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, 3,4,5-trimethoxymethylbenzoate has a broader market prospect. Therefore, it is possible to produce 3,4,5-trimethoxymethylbenzoate simply and efficiently There are great social benefits. [0003] At present, the preparation method commonly used in industry is: use gallic acid as raw material, carry out methy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/31C07C69/92
CPCC07C67/08C07C67/31C07C69/92C07C69/84
Inventor 杨彦明陈波王文龙赵国锋
Owner JIURUI BIOLOGY & CHEM CO LTD
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