Process for producing asarin

A technology of Asarum and Lewis acid, which is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of high-temperature distillation, high anhydrous requirements, and inconvenient production.

Inactive Publication Date: 2009-07-29
亚邦化工集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This route uses Grignard reagent in the process of making from 3 to 4. Because the Grignard reagent has high requirements for anhydrous production equipment and uses flammable solvents such as ether or tetrahydrofuran, not only that, but also requires high vacuum distillation, which brings many problems to production. inconvenient
[0006] Liu Bochun's patent (publication number CN1511817A) reported that 1,2,4-trimethoxybenzene was used as raw material to obtain 2,4,5-trimethoxybenzaldehyde through VILSMEIER reaction, and the latter was dehydrated with propionic anhydride and sodium propionate to prepare the product , but high-temperature distillation is required, and the yield has not been clearly reported

Method used

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  • Process for producing asarin
  • Process for producing asarin
  • Process for producing asarin

Examples

Experimental program
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Effect test

Embodiment 1

[0031] One, the preparation of 2,4,5-trimethoxypropiophenone

[0032] Put 15 kg of 1,2,4-trimethoxybenzene, 15 kg of propionic anhydride, and 300 kg of dichloromethane into the kettle, lower the temperature to 15°C, add 26 kg of aluminum trichloride, and keep the temperature below 30°C. After the addition, the temperature was raised to 40-70°C, and the heat preservation reaction was carried out for 2-5 hours. The material was discharged into 400 kg of water, extracted with dichloromethane (100 liters × 3), the organic layers were combined, washed with water until neutral, and dichloromethane was distilled under normal pressure. methane, placed at room temperature for crystallization, filtered, and dried under normal pressure. 15 kg of solid was obtained, the yield was 75%. The melting point is 107-109°C.

[0033] Two, the preparation of 2,4,5-trimethoxyphenylpropanol

[0034] Dissolve 15 kg of the reaction product of the previous step in 100 liters of tetrahydrofuran, cool ...

Embodiment 2

[0038] One, the preparation of 2,4,5-trimethoxypropiophenone

[0039] Put 15 kg of 1,2,4-trimethoxybenzene, 15 kg of propionyl chloride, and 300 kg of dichloroethane into the kettle, lower the temperature to 15°C, add 26 kg of aluminum trichloride, and keep the temperature below 30°C. After the addition, the temperature is raised to 40-70°C, the reaction is kept for 2-5 hours, and the material is discharged into 400 kg of water. Extract with dichloroethane (100 liters x 3), combine organic layers, wash with water until neutral, evaporate dichloroethane under normal pressure, place at room temperature for crystallization, filter, and dry under normal pressure. 14.4 kg of solid was obtained with a yield of 72%. The melting point is 107-109°C.

[0040] Two, the preparation of 2,4,5-trimethoxyphenylpropanol

[0041] Dissolve 15 kg of the reaction product of the previous step in 100 kg of ethyl acetate, cool in an ice-salt bath to -5°C, start adding sodium borohydride, after the...

Embodiment 3

[0045] One, the preparation of 2,4,5-trimethoxypropiophenone

[0046] Put 15 kg of 1,2,4-trimethoxybenzene, 26 kg of anhydrous zinc chloride, and 300 kg of dichloroethane into the kettle, lower the temperature to 20°C, add 15 kg of propionic anhydride dropwise, and keep the temperature below 30°C. After the addition, the temperature is raised to 60°C, and the reaction is kept for 2-5 hours, and the material is discharged into 400 kg of water. The layers were separated, the aqueous layer was extracted with dichloromethane (100 liters × 3), the organic layers were combined, washed with water until neutral, dichloromethane was evaporated under normal pressure, crystallized, filtered, and dried under normal pressure. 16 kg of solid was obtained with a yield of 78%. The melting point is 107-109°C.

[0047] Two, the preparation of 2,4,5-trimethoxyphenylpropanol

[0048]Dissolve 15 kg of the reaction product of the previous step in 100 kg of ethyl acetate, cool in an ice-salt bath...

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Abstract

As during the process of preparing asarin from 1, 2, 4-trimethoxybenzene, the raw materials of propionic anhydride, propionyl chloride, anhydrous aluminum chloride, anhydrous zinc chloride, dichloromethane, sodium borohydride, sodium propionate and the like with low prices are used, the production cost is lowered greatly. At the same time, the post treatment of the invention is convenient; products of each step are all solids which are convenient for detecting; the reaction yield of each step is high; and the production process generates few three wastes. In conclusion, in the invention, the 1, 2, 4-trimethoxybenzene which is obtained easily in China is used as a raw material to prepare the asarin by the reactions such as acidylation and the like; the invention has low cost, safe and simple operation, high reaction yield and less environmental pollution; and compared with the existing reported method, the invention is fit for the industrialized production better.

Description

technical field [0001] The invention relates to a preparation method of a-asarone crude drug for cough and expectorant. Background technique [0002] Asarone is the active ingredient in the volatile oil of Shichangpu, and its chemical name is: E-2,4,5-trimethoxy-1-propenylbenzene. After extraction, separation and pharmacological studies, it has been found that it has pharmacological effects such as asthma, expectorant, cough, sedation, and anti-inflammatory. Acute and chronic bronchitis, bronchitis, bronchial asthma, and pneumonia caused by respiratory tract infection. [0003] People such as Wang Zhicai (organic chemistry, 1990,10,350-352) take 1,2,4-trimethoxybenzene (2) as raw material, react and generate 2,4,5-trimethoxybenzaldehyde (3), and then Then react with the Grignard reagent ethylmagnesium bromide to generate 2,4,5-trimethoxyphenylpropanol (4), and then dehydrate 4 to generate the target product 1. The reaction process is as follows: [0004] [0005] This ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/205C07C41/30
Inventor 石卫兵黄书卷孙毅
Owner 亚邦化工集团有限公司
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