Green and environment-friendly method for synthesizing veratraldehyde

A green and environmentally friendly veratraldehyde technology, applied in chemical instruments and methods, condensation preparation of carbonyl compounds, physical/chemical process catalysts, etc., can solve the problem of difficult control of chlorination process, easy generation of monochlorine and trichlorine by-products, conversion The efficiency and purity are not high, so as to overcome the difficulty of catalyst separation, reduce the environmental protection and biochemical intensity, and avoid the effect of low production yield.

Active Publication Date: 2022-05-06
宁夏宁泰科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many techniques for synthesizing veratraldehyde, and the main synthetic methods at present include: (1) taking vanillin as a synthetic method for raw material to carry out methylation, conventional methylation reagents include dimethyl sulfate, dimethyl carbonate etc., the price of the methylation reagent is not only high, but also in the reaction process, only a part of methyl ester can participate in the methylation, and the active ingredient of the molecule is also low, which is not conducive to cost control. The wastewater of methyl ester or monomethyl carbonate causes great pollution to the environment; (2) with veratrole as raw material, hydrocyanic acid is first cyanided and then hydrolyzed, and this process involves highly toxic hydrocyanic acid, or chloroform Sommelet reaction is carried out again after alkylation, and this technique is easy to polymerize, so by-product is more, and conversion rate and purity are not high; Process The chlorination process is difficult to control, and it is easy to generate monochlorine and trichlorine by-products

Method used

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  • Green and environment-friendly method for synthesizing veratraldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] A kind of green environment-friendly method for synthesizing veratraldehyde, comprises the following steps:

[0034] S1. Add vanillin, 1-methoxy-2,2,6,6-tetramethylpiperidine and cesium carbonate to toluene, heat up to 70° C., stir and keep warm for 8 hours;

[0035] The preparation method of the 1-methoxy-2,2,6,6-tetramethylpiperidine is:

[0036] Weigh 5.0 g of 2,2,6,6-tetramethylpiperidin-1-oxyl radical (CAS No.: 2564-83-2) and dissolve it in cold dimethyl sulfoxide solution, mix well Add 12.2g of ferrous sulfate heptahydrate, add 18mL of 30% hydrogen peroxide solution drop by drop under ice-water bath and stirring conditions, keep stirring for 1 hour after the addition is completed, and add 100mL of deionized water after the reaction is completed Dilute, then extract with ether, take the organic phase, wash with brine, dry over anhydrous sodium sulfate, concentrate, and purify by silica gel chromatography (500 mesh), eluting with ethyl acetate-hexane (v / v=1:19) , ...

Embodiment 2

[0040] A kind of green environment-friendly method for synthesizing veratraldehyde, comprises the following steps:

[0041] S1. Add vanillin, 1-methoxy-2,2,6,6-tetramethylpiperidine and barium hydroxide to toluene, heat up to 70°C, stir and keep warm for 8 hours;

[0042] The preparation method of the 1-methoxy-2,2,6,6-tetramethylpiperidine is the same as in Example 1;

[0043] The mass ratio of the toluene to the vanillin, the 1-methoxy-2,2,6,6-tetramethylpiperidine and the barium hydroxide is 10:1:1.2:0.6;

[0044] S2, after the stirring reaction is completed, the reaction system is washed with deionized water, the organic layer is collected, and the toluene is evaporated to obtain veratraldehyde. Through gas chromatography analysis, the purity of the reveratrol product is 97.5%, and the yield is 95.6%.

Embodiment 3

[0046] A kind of green environment-friendly method for synthesizing veratraldehyde, comprises the following steps:

[0047] S1. Add vanillin, 1-methoxy-2,2,6,6-tetramethylpiperidine and a porous carbon material loaded with cesium carbonate into toluene, heat up to 70° C., stir and keep warm for 8 hours;

[0048] The preparation method of the 1-methoxy-2,2,6,6-tetramethylpiperidine is the same as in Example 1;

[0049] The preparation method of the porous carbon material loaded with cesium carbonate is:

[0050] (1) Template preparation

[0051] Weigh 3g of P123 and dissolve it in 20mL of absolute ethanol, fully dissolve and mix, add 0.13g of cesium nitrate, mix again, add dropwise 6.2g of tetraethyl orthosilicate and 0.7mL of hydrochloric acid solution (1mol / L) while stirring , after the dropwise addition, let it stand, evaporate the solvent and perform heat preservation and heat treatment at 580-650 ° C to obtain a doped SBA template;

[0052] (2) Weigh 2.5g of glucose and...

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Abstract

The invention provides a green and environment-friendly method for synthesizing veratraldehyde, which belongs to the technical field of spice intermediate synthesis, and comprises the following steps: S1, adding vanillin, a methylation reagent and a catalyst into a reaction solvent, heating, stirring, and carrying out heat preservation reaction; wherein the methylation reagent is 1-methoxy-2, 2, 6, 6-tetramethylpiperidine or 1-methoxy-4-hydroxy-2, 2, 6, 6-tetramethylpiperidinol, and the catalyst comprises at least one of an oxide, a hydroxide and a carbonate of Cs or Ba, and the catalyst comprises at least one of an oxide, a hydroxide and a carbonate of Cs or Ba. S2, after the stirring reaction is completed, washing with deionized water, collecting an organic layer, and evaporating to remove a reaction solvent to obtain veratraldehyde; according to the invention, the synthesis process is simplified, and the defects of low production yield, more byproducts, difficulty in separation and the like are avoided.

Description

technical field [0001] The invention relates to the technical field of synthesis of perfume intermediates, in particular to an environmentally friendly method for synthesizing veratraldehyde. Background technique [0002] Veratraldehyde, that is, 3,4-dimethoxybenzaldehyde (3,4-DIMETHOXYBENZALDEHYDE), also known as pyrocatechin aldehyde dimethyl ether, the appearance is white or light yellow flaky crystals, melting point 42-45 ℃, boiling point 281-285°C; slightly soluble in hot water, easily soluble in ethanol and ether; sensitive to air; the solution can be oxidized to 3,4-dimethoxybenzoic acid under the influence of light, with vanilla fruit and jasminal The fragrance is mainly used in the perfume industry, and can also be used in the synthesis of pharmaceutical intermediates, the drug methyldopa, the veterinary sulfa synergist Dibendil, and the synthesis of antibiotics. [0003] Veratraldehyde has a wide range of uses, and the market demand is increasing year by year and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/45C07C47/575B01J27/236B01J35/10C07D211/94C07D211/40
CPCC07C45/45B01J27/236B01J35/10C07D211/94C07D211/40C07C47/575Y02P20/584
Inventor 王晶甄立岗戚祥开欣苏柳宇王瑞枫
Owner 宁夏宁泰科技有限公司
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