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Method for preparing dimethoxy benzaldehyde from veratrole

A technology of ortho-veratraldehyde and veratrol, which is applied in the field of preparation of chemical drug intermediates, can solve the problems of environmental pollution, high purchase cost, unfriendly environment, etc., and achieve the reduction of environmental toxicity, cheap and easy-to-obtain raw materials, and the process easy effect

Active Publication Date: 2013-07-10
ZHANG JIA GANG VINSCE BIO PHARM
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

Although this method overcomes many shortcomings such as high reagent toxicity, high equipment requirements, unfriendly environment, catalyst consumption, equipment corrosion, and complicated post-treatment procedures in the traditional process, it still has high reaction temperature and strict control over reaction conditions. Harsh and other problems, not suitable for industrial production
[0005] Because o-vanillin itself is an important intermediate in the synthesis of chemical drugs, its purchase cost is relatively high, and there are problems of high cost and uneconomical when used as raw materials for industrial production, and there are some problems in the existing technology such as equipment High requirements, high toxicity, environmental pollution, mild conditions and other factors are not conducive to industrial production. Therefore, it is currently the main method to provide an economical, mild condition, high yield, good quality, and low energy consumption suitable for industrial production. research direction

Method used

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  • Method for preparing dimethoxy benzaldehyde from veratrole

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 13.8g of veratrole into a 250mL glass three-necked flask, start stirring, add 7g of sodium trifluoromethanesulfonate as catalyst, add 16mL of 35% hydrochloric acid solution dropwise, add 8ml of glyoxylic acid dropwise, heat up to 70°C after adding, and react 8h. After the reaction, the reaction liquid was cooled, and 100 ml of water and 100 ml of petroleum ether were added for extraction, and the lower aqueous layer was separated. Add 8ml of acetic acid dropwise to the upper layer, add 20g of urotropine, stir and react at room temperature for 2h, wash the reaction solution with water, let it stand for layering, take the organic phase and concentrate under reduced pressure, and after cooling, o-veratraldehyde crystals are obtained. Yield 85%, purity 95.0% (GC).

Embodiment 2

[0029] Add 13.8g of veratrole into a 250mL glass three-necked flask, start stirring, add 7g of sodium trifluoromethanesulfonate as catalyst, add 16mL of 35% hydrochloric acid solution dropwise, add 8ml of glyoxylic acid dropwise, heat up to 70°C after adding, and react 5h. After the reaction, the reaction liquid was cooled, and 100 ml of water and 100 ml of petroleum ether were added for extraction, and the lower aqueous layer was separated. Add 8ml of acetic acid dropwise to the upper layer, add 20g of urotropine, stir and react at room temperature for 2h, wash the reaction solution with water, let it stand for layering, take the organic phase and concentrate under reduced pressure, and after cooling, o-veratraldehyde crystals are obtained. Yield 82%, purity 65.5% (GC).

Embodiment 3

[0031] Add 13.8g of veratrole into a 250mL glass three-necked flask, start stirring, add 7g of catalyst sodium trifluoromethanesulfonate, add 16mL of 35% hydrochloric acid solution dropwise, add dropwise 8ml of glyoxylic acid, heat up to 50°C after the addition, and react 10h. After the reaction was completed, the reaction liquid was cooled, and 50 ml of water and 50 ml of petroleum ether were added for extraction, and the lower aqueous layer was separated. Add 8ml of acetic acid dropwise to the upper layer, add 20g of urotropine, stir and react at room temperature for 2h, wash the reaction solution with water, let it stand for layering, take the organic phase and concentrate under reduced pressure, and after cooling, o-veratraldehyde crystals are obtained. Yield 85%, purity 94.8% (GC).

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Abstract

The invention relates to a preparation method of an important medical intermediate product dimethoxy benzaldehyde. A dimethoxy benzaldehyde crystal is prepared from veratrole through a substitution reaction and an oxidizing reaction by treatment. The process disclosed by the invention has the advantages of easily available raw material, economical efficiency, applicability, moderate condition, high yield, good quality, low energy consumption and the like, and is applicable to industrial production.

Description

technical field [0001] The invention relates to the preparation of chemical medicine intermediates, in particular to a preparation method of o-veratraldehyde, which is a preparation method of chemically synthesizing o-veratraldehyde with veratrol as raw material. Background technique [0002] O-veratraldehyde (o-veratraldehyde), also known as 2,3-dimethoxybenzaldehyde, CAS NO.86-51-1, its chemical name is 2,3-Dimethoxybenzaldehyde, molecular formula is C 9 h 10 o 3 , the molecular weight is 166.18. Colorless or white needle crystal, insoluble in water, soluble in ethanol, melting point is 51-53℃. Ortho-veratraldehyde, as a raw material for pharmaceutical chemical synthesis, is mainly used in the synthesis of berberine. In recent years, with the development of downstream product technology, it has become more and more widely used. [0003] At present, there are few techniques for producing o-veratraldehyde at home and abroad. The product mainly comes from the by-product ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/575C07C45/28
Inventor 彭学东张梅赵金召弓旻
Owner ZHANG JIA GANG VINSCE BIO PHARM
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