Method for preparing caffeic acid phenethyl ester

The technology of phenethyl caffeate and phenethyl acetate is applied in the field of preparation of phenethyl caffeate, can solve the problems of high price of triphenylphosphine, complicated reaction steps, short reaction time, etc., and achieves the advantages of few steps and easy Controlled, low-cost effects

Inactive Publication Date: 2012-10-24
湖北远成赛创科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Method 1 caffeic acid and phenethyl ester directly catalyze the synthesis of CPAE, the reaction conditions are simple, but time-consuming and low yield
Method 2 The acid chloride esterification method has mild reaction conditions, short reaction time, and high yield, but the acylating agent used is severely corroded and causes great environmental pollution.
Method 3: Alkali-catalyzed reaction between halogenated hydrocarbons and acids, the conditions are mild, but most of the reaction time is long and the operation is cumbersome
Method 4 has short reaction time and high yield, but the triphenylphosphine used is expensive and causes great environmental pollution
Method 5 adopts malonate method, the reaction steps are complicated, and there are many side reactions

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Add 55 g of 0.4 mol of 3,4-dihydroxybenzaldehyde and 98 g of 0.6 mol of phenylethyl acetate into a reactor filled with 450 g of absolute ethanol, stir and mix until all the raw materials are dissolved. Then 3.75 g of a solution of sodium ethoxide in absolute ethanol with a mass fraction of 20% was added. The reaction was carried out under stirring at room temperature for 2 hours by microwave irradiation. Microwave power 500W. After the reaction was completed, most of the solvent anhydrous ethanol was evaporated by rotary evaporation, and the evaporation was stopped when solids were precipitated. After the residue was cooled, ice water was added while stirring, and filtered after thorough stirring. The obtained solid was recrystallized with toluene to obtain a pure product. The purity is 99%, and the yield is 86%.

Embodiment 2

[0016] Add 110 g of 0.8 mol of 3,4-dihydroxybenzaldehyde and 220 g of 1.35 mol of phenethyl acetate into a reactor filled with 330 g of absolute ethanol, stir and mix until all the raw materials are dissolved. Then 12 g of a solution of sodium methoxide in absolute ethanol with a mass fraction of 30% was added. The reaction was carried out under stirring at room temperature for 1.5 hours by microwave irradiation. Microwave power 550W. After the reaction is completed, most of the solvent anhydrous ethanol is evaporated by rotary evaporation, and the evaporation is stopped when solids are precipitated. After cooling, add ice water while stirring, and filter after fully stirring. The obtained solid hot toluene is cooled and crystallized to obtain caffeic acid phenylethyl alcohol with a purity of 99%. Ester, yield 85%.

Embodiment 3

[0018] Add 70 g of 0.5 mol of 3,4-dihydroxybenzaldehyde and 160 g of 1.0 mol of phenylethyl acetate into a reactor filled with 460 g of absolute ethanol, stir and mix until all the raw materials are dissolved. Then 23 g of anhydrous ethanol solution of potassium ethylate with a mass fraction of 20% was added. The reaction was stirred at room temperature for 1 hour by microwave irradiation. Microwave power 600W. After the reaction is completed, most of the solvent anhydrous ethanol is evaporated by rotary evaporation, and the evaporation is stopped when solids are precipitated. After cooling, add ice water while stirring, and filter after fully stirring. The obtained solid hot toluene is cooled and crystallized to obtain caffeic acid phenylethyl alcohol with a purity of 98%. Ester, yield 88%.

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PUM

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Abstract

The invention provides a method for preparing caffeic acid phenethyl ester. The method comprises steps that 3, 4-dihydroxy benzaldehyde and phenylethyl acetate are subjected to microwave irradiation for 1 to 2 hours under catalysis of an organic base in a protic organic solvent to synthesize the caffeic acid phenethyl ester. According to invention, the method has advantages of simple technology, one-step synthesis, cheap and easily-available raw materials, non-toxic sodium alkoxide catalyst and low synthesis cost, the reaction can be carried out at room temperature, a yield is more than 85%, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a preparation method of phenethyl caffeate. Background technique [0002] Propolis has a wide range of plant sources, and its chemical composition is extremely complex. So far, more than 20 types and more than 300 chemical components have been identified from propolis, mainly including flavonoids, phenolic acids, terpene acids, steroids, and amino acids. substances, etc. Among the many functional components of propolis, caffeic acid phenylethyl ester (CPAE) has been identified as one of the main active components in propolis, and many biological activities of propolis are related to CPAE. Phenylethyl caffeate has various pharmacological activities such as anti-oxidation, anti-virus, DNA inhibition, apoptosis induction, anti-bacterial, anti-inflammatory, anti-arteriosclerosis and immunity enhancement, etc. It has broad application prospects in food, medicine and other fields. [00...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/732C07C67/343
Inventor 叶思朱如慧杨启伟周艳丽
Owner 湖北远成赛创科技有限公司
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