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Synthesis method of hellebore aldehyde

A synthetic method, the technology of veratraldehyde, applied in the field of synthesizing veratraldehyde, can solve the problems of high pollution, low yield, limiting the use efficiency of reactors, etc., and achieve the effect of less industrial waste water and low cost

Inactive Publication Date: 2013-07-10
JIAXING EPOCHEM PHARMTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The product synthesized by this method not only has a low yield (about 10%), but also needs to use an organic solvent as the reaction medium for the reaction, which limits the efficiency of the reactor.
Also due to the large amount of AlCl used 3 (For example: 110 kg of veratrole requires 192 kg of aluminum trichloride) is a highly polluting chemical raw material, and the used formylating reagent N, N-dimethylformamide (DMF) will also cause excessive reagents that cannot be recovered

Method used

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  • Synthesis method of hellebore aldehyde
  • Synthesis method of hellebore aldehyde
  • Synthesis method of hellebore aldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Methylation Reaction-Synthesis of Veratrole

[0029] 110 kilograms (1kmmol) of catechol and 120 kilograms of dimethyl sulfate are added to the reactor, and 300 kilograms of distilled water are added. Under stirring condition, add 184.8 kilograms (2.2kmol) sodium bicarbonate in batches, until completely no bubbles are produced. The reaction system was cooled to -5°C. Pass about 151.5 kg (3 kmol) of dichloromethane into the reaction system, and seal the reaction system. React under 80 degree steam bath for 12 hours. Cool to room temperature and open the reaction kettle. Separate the organic layer. The aqueous layer was extracted once with dichloroethane. The organic layers were combined and dried over anhydrous sodium sulfate. Dichloroethane was recovered by atmospheric distillation, and 125 kg of product was obtained by vacuum distillation (90% yield). The results of elemental analysis of veratrole showed: C, 69.54; H, 7.30; O, 23.16; H NMR spectrum data: δ(CDCl3)...

Embodiment 2

[0035] Methylation Reaction-Synthesis of Veratrole

[0036]110 kilograms (1kmmol) of catechol and 122 kilograms (1kmmol) of methyl iodide were added to the reactor, and 200 kilograms of distilled water and 100 kilograms of acetone were added. Under stirring condition, add 233.2 kilograms (2.2kmol) sodium carbonate in batches, produce completely without bubble. The reaction system was cooled to 0°C. About 151.5 kg (3 kmol) of dichloromethane was introduced into the reaction system. Closed reaction system. React for 12 hours in a steam bath. Cool to room temperature and open the reaction kettle. Separate the organic layer. The aqueous layer was extracted once with dichloroethane. The organic layers were combined and dried over anhydrous sodium sulfate. Dichloroethane was recovered by atmospheric distillation, and 110 kg of product was obtained by vacuum distillation (yield 80%). Elemental analysis data: C, 69.54; H, 7.30; O, 23.16; H NMR spectrum data: δ(CDCl3): 6.88(s, ...

Embodiment 3

[0042] Methylation Reaction-Synthesis of Veratrole

[0043] 110 kilograms (1kmmol) of catechol and 122 kilograms (1kmmol) of methyl iodide were added to the reactor, and 200 kilograms of distilled water and 100 kilograms of acetone were added. Under stirring condition, add 233.2 kilograms (2.2kmol) sodium carbonate in batches, produce completely without bubble. The reaction system was cooled to -3°C. About 151.5 kg (3 kmol) of dichloromethane was introduced into the reaction system. Closed reaction system. React for 12 hours under steam bath. Cool to room temperature and open the reaction kettle. Separate the organic layer. The aqueous layer was extracted once with dichloroethane. The organic layers were combined and dried over anhydrous sodium sulfate. Dichloroethane was recovered by atmospheric distillation, and 110 kg of product was obtained by vacuum distillation (yield 80%). Elemental analysis data: C, 69.54; H, 7.30; O, 23.16. H NMR spectrum data: δ(CDCl3): 6.88...

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Abstract

The invention discloses a hellebore aldehyde synthetic method. The method comprises the following steps of: synthesizing veratrole through methylation reaction by using pyrocatechol as a material; and synthesizing N-methylformanilide through formylation reaction using N-methylaniline as a material; reacting veratrole with N-methylformanilide at 20-100 DEG C for 8-24 h in the presence of a condensing agent and a catalyst to prepare the product with the purity of more than 97%. The invention is a clean and efficient synthesis method, the cost of the materials used in the invention is low, the formylation reagent can be recycled, and the industrial wastewater is less.

Description

technical field [0001] The invention relates to a method for synthesizing a pharmaceutical intermediate, in particular to a method for synthesizing veratraldehyde by using catechol and N-methylaniline as raw materials. Background technique [0002] Veratraldehyde is an important synthetic spice and pharmaceutical intermediate, which can be used to synthesize methyldopa, veratronic acid, etc. The starting material of the new drug Aliskiren (Aliskiren) launched by Novartis recently is isovanillin, which is demethylated by veratraldehyde and then synthesized. Synthesizing veratraldehyde from vanillin is a relatively classic synthesis method, which is mostly used in industrial production. However, in recent years, the price of vanillin has soared, and the profit margins of enterprises have become thinner and thinner, so it is necessary to explore a new process for the synthesis of veratraldehyde. Chinese invention patent application CN101434523A discloses a chemical synthesis ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C47/575C07C45/45
Inventor 葛承胜韩志唐飞宇王小东
Owner JIAXING EPOCHEM PHARMTECH
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