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Preparing method for veratrole

A technology of veratrol and a catalyst is applied in the field of preparation of chemical drug intermediates, can solve the problems of human body and environmental hazards, consumption of lye, low yield and the like, and achieves the effects of environmental friendliness and simple process.

Active Publication Date: 2017-03-22
ZHANG JIA GANG VINSCE BIO PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the methylation reaction using catechol and dimethyl sulfate is the most commonly used method in industry, such as patent number 201210405038.8 (a preparation process of veratrole), because dimethyl sulfate is a highly toxic chemical , A little carelessness during use will cause great harm to the human body and the environment
At the same time, sulfuric acid is generated during the reaction, which seriously corrodes the equipment and consumes a large amount of lye, which also increases the difficulty of separation and purification.
Another method is to use catechol to react with sodium hydroxide to generate sodium salt, and then react with methyl chloride under a certain pressure to obtain the finished product, such as Patent No. 201010161432.2 (synthesis method of phthalic dimethyl ether), for the reaction The condition control is relatively strict and the yield is not high
How to solve the problems of the feasibility and ease of operation of industrialized large-scale production, reduce environmental pollution, and reduce production costs are the main research directions at present. Prior to this, the application number of Zhangjiagang Weisheng Biomedicine Co., Ltd. is provided in 2013100826229 A new preparation method of veratrol, but its yield still can not reach 99%

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] This example provides a kind of preparation method of veratrole, concrete implementation is as follows:

[0020] At 0°C, put 300ml of aqueous solution in a 500ml glass three-necked flask, then add 140ml of dimethyl carbonate, start stirring, add 110g of catechol, add 4g of catalyst benzyltrimethylammonium chloride, and dropwise add liquid caustic soda , control the pH of the reaction system between 8 and 9, then raise the temperature in the reaction vessel to 30°C within 1.5h, and keep it warm for 0.5h, then raise the temperature to 80°C within 1h, keep it warm for 1h, and then heat it up for 2h Internally raise the temperature to 100°C, keep it warm for 1.5h, and then continue to heat up to reflux. After the reflux, stand for 1h until the layers are separated, remove the lower water layer, add liquid alkali to the oil layer for washing, and obtain 148g of crude oil, and then The crude oil was distilled under reduced pressure to obtain 137.0 g of pure product with a yie...

Embodiment 2

[0022] This example provides a kind of preparation method of veratrole, concrete implementation is as follows:

[0023] At 5°C, put 300ml of aqueous solution in a 500mL glass three-necked flask, then add 125mL of dimethyl carbonate, start stirring, add 110g of catechol, add 3.3g of catalyst benzyltrimethylammonium chloride, and add dropwise Alkali, control the pH of the reaction system between 8 and 9, then raise the temperature in the reaction vessel to 40°C within 1.5h, keep it warm for 1h, then raise the temperature to 75°C within 1.5h, keep it warm for 1h, and then Heat up to 100°C within 1.5h, keep warm for 1h, then continue to heat up to reflux, after the reflux, stand for 1h until the layers are separated, remove the lower water layer, add liquid alkali to the oil layer for washing, and obtain 145g of crude oil, then The crude oil was distilled under reduced pressure to obtain 136.8 g of pure product with a yield of 99.1% and a purity of 99.8% (GC).

Embodiment 3

[0025] This example provides a kind of preparation method of veratrole, concrete implementation is as follows:

[0026] At 5°C, put 300ml of aqueous solution in a 500mL glass three-necked flask, then add 140mL of dimethyl carbonate, start stirring, add 110g of catechol, add 2.5g of catalyst benzyltrimethylammonium chloride, and add dropwise Alkali, control the pH of the reaction system between 8~9, then raise the temperature in the reaction vessel to 35°C within 2 hours, keep it warm for 0.5h, then raise the temperature to 80°C within 1h, keep it warm for 0.5h, and then in the Heat up to 100°C within 2 hours, keep warm for 1 hour, then continue to heat up to reflux, after the reflux, let stand for 1.5 hours until the layers are separated, remove the lower water layer, add liquid alkali to the oil layer for washing, and obtain 142g of crude oil, and then The crude oil was distilled under reduced pressure to obtain 136.7 g of pure product with a yield of 99.1% and a purity of 99...

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PUM

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Abstract

The invention discloses a preparing method for veratrole. In the method, catechol and dimethyl carbonate are taken as raw materials and are subjected to reaction under a catalyst condition to produce veratrole. The method comprises the following specific progress: under the temperature condition of 0-5 DEG C, adding catechol and diethyl carbonate into a water solution, starting stirring and adding a catalyst, gradually heating to 100 DEG C, controlling the reaction system at a pH of 8-9 during reaction and then continuing to heat to reflux; after reflux is finished, performing standing and layering, adding liquid caustic soda into the oil phase, and performing washing, so as to obtain crude oil; and at last performing reduced-pressure distilling on the crude oil, so as to obtain a pure product veratrole. The catalyst is benzyltrimethylammonium chloride. The yield of veratrole prepared by the method is as high as 99% or more and the purity is as high as 99.5% or more. Furthermore, the whole manufacturing technique has the characteristics of low cost, environment friendliness and cleanness and safety.

Description

technical field [0001] The invention relates to the preparation of chemical drug intermediates, in particular to a preparation method of veratrole. Background technique [0002] Veratrole, also known as o-dimethyl ether, CAS NO. 91-16-7, its chemical name is 1,2-dimethoxybenzene, its molecular formula is C8H10O2, and its molecular weight is 138.16. Colorless liquid or crystal, soluble in ethanol, ether and fatty oil, slightly soluble in water, melting point is 15°C. As a raw material for pharmaceutical chemical synthesis, veratrole has a wide range of industrial applications, is an important fine chemical raw material, and is also a synthetic flavor and one of the important raw materials in the field of medicine. Mainly used for the synthesis of o-veratraldehyde, tetrahydropalmatine, verapamil, determination of lactic acid in blood, determination of glycerol, etc. At present, there are few reports on the preparation process of veratrole. Most of them use catechol or gua...

Claims

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Application Information

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IPC IPC(8): C07C41/16C07C43/205
CPCC07C41/16C07C43/2055
Inventor 张梅彭学东赵金召闫勇义
Owner ZHANG JIA GANG VINSCE BIO PHARM
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