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Novel method for synthesizing alpha-asarone

A technology of asarone and trimethoxybenzene, which is applied in the new synthesis field, can solve the problems of cumbersome operation, high cost, and low yield of α-asarone, and achieve the effect of simple operation and improved production yield

Inactive Publication Date: 2008-06-11
广西中医学院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The purpose of this invention is to provide a new synthetic route that does not need to prepare propionic acid chloride, and can directly obtain all-trans α-asarone without separation, which can solve the problem that the yield of synthesizing α-asarone is not high at present, Expensive, or use of toxic organic solvents, cumbersome operations, etc.

Method used

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  • Novel method for synthesizing alpha-asarone
  • Novel method for synthesizing alpha-asarone
  • Novel method for synthesizing alpha-asarone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Add 4 grams of anhydrous zinc chloride to the dry reaction flask, add 30 ml of phosphorus oxychloride, and stir the reaction at 50°C, then add 1.04 grams of propionic acid and 1.68 grams of 1,2,4-trimethoxybenzene, and stir the reaction After 1 to 5 hours, the end point of the reaction was detected by TLC, cooled with ice water, and stirred until solids were precipitated. Filter, wash with water until neutral, and dry to obtain 2 g of off-white small needle crystal product. The yield was 89.29% (based on 1,2,4-trimethoxybenzene), and the product was recrystallized from methanol for use. m.p106-108°C.

Embodiment 2

[0057] Add 10 grams of anhydrous zinc chloride (or anhydrous aluminum trichloride) in the dry reactor, add 25 milliliters of phosphorus oxychloride and sodium polyphosphate (or monopotassium hydrogen phosphate or potassium dihydrogen phosphate), Stir the reaction at 30°C, then add 2.3 grams of propionic acid and 3.36 grams of 1,2,4-trimethoxybenzene, stir the reaction for 1 to 5 hours, check the end point of the reaction with TLC, cool with ice water, and stir until the solid precipitates. Filter, wash with water until neutral, and dry to obtain 3.9 g of an off-white product with a yield of 87.05%. Recrystallize with methanol to obtain a small needle crystal product, which is dried for use.

Embodiment 3

[0059] Add 15 grams of anhydrous zinc chloride to the dry reaction bottle, add 40 ml of phosphorus oxychloride (or phosphoric acid), and an appropriate amount of potassium dihydrogen phosphate or dipotassium hydrogen phosphate or potassium phosphate, stir the reaction at 70 ° C, and then add 3.7 grams of propionic acid and 5.04 grams of 1,2,4-trimethoxybenzene were stirred and reacted for 1 to 5 hours, and the end point of the reaction was detected by TLC, cooled with ice water, and stirred until solids were precipitated. Filter, wash with water until neutral, and dry to obtain 5.8 g of small needle crystal product with a yield of 86.31%. The product is recrystallized with methanol and dried for use.

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Abstract

The invention relates to a method for synthesizing alpha-Asarone, which uses hydroquinone as raw material to synthesize 1, 2, 4-trimethoxybenzene through oxidizing, triacetylizing and methylating and is characterized in using 1, 2, 4-trimethoxybenzene as raw material to prepare alpha-Asarone through directly propionylating reaction of propionic acid, reduction and dehydration. The raw material of each step in the synthesizing path of alpha-Asarone is easily obtained without using toxic organic solvent and the product needn't separate to obtain alpha-Asarone directly and the production the yield is improved greatly. The total yield reaches 65%-86%, the purity reaches over 98%, further the operation is simple and the post-treatment problem of propionylated mother liquid is solved.

Description

technical field [0001] The present invention relates to a new synthesis method of α-asarone. Background technique [0002] α-asarone (asarone; α-asarone; asarin; asarum camphor), also known as α-asarone, chemical name (E)-2,4,5-trimethoxy-1-propenylbenzene, the earliest Found in the volatile oil of Araceae plant Acorus gramineus soland. Since the 1960s, extensive research has been carried out on α-asarone at home and abroad. Foreign countries focus more on toxicology and chemical synthesis, while domestic research mainly focuses on clinical application. "Dictionary of Traditional Chinese Medicine" edited by Jiangsu New Medical College, People's Publishing House, Shanghai, 1977, p612 and "Chinese Herbal Medicine Newsletter" 1978, 241, the Chinese Anesthesia Research Group of Nanjing School of Pharmacy, and Wu Chuang in the "Research Progress of α-Asarone", "Chinese Journal of Pharmaceutical Sciences", 1997, 32(3): 129 has confirmed that α-asarone has strong pharmacological ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/205C07C41/30
Inventor 陈毅平
Owner 广西中医学院
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