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Process for synthesizing chalcone and derivates thereof by using ion liquid

An ionic liquid and chalcone technology, which is applied in the synthesis field of producing chalcone and its derivatives, can solve the problems of complicated separation and purification, and achieve the effect of easy separation process

Inactive Publication Date: 2008-10-22
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The extensive use of traditional strong acids, strong bases and organic solvents complicates the subsequent separation and purification of the reaction

Method used

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  • Process for synthesizing chalcone and derivates thereof by using ion liquid
  • Process for synthesizing chalcone and derivates thereof by using ion liquid
  • Process for synthesizing chalcone and derivates thereof by using ion liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Add 3.58g (0.01mol) ionic liquid 3-butyl-1-(butyl-4-sulfonic acid) imidazolium bisulfate, 6.01g (0.05mol) acetophenone, 5.31g (0.05mol) benzaldehyde In a three-necked flask equipped with a stirrer, a thermometer, and a reflux condenser, stir and raise the temperature to 140°C, and react for 6 hours. After the reaction solution is allowed to stand and separate, the chalcone product in the upper layer is poured out, recrystallized and purified, 1,3- The yield of diphenyl-2-propen-1-one (chalcone) is 96.9%, and the selectivity is 99.8%. The lower ionic liquid was dried in vacuum at 110 °C for 2 h and reused.

Embodiment 2-10

[0037] Embodiment 2-10: the specific experimental process is similar to embodiment 1

[0038] Reality

Embodiment 11-13

[0040] 6.01g (0.05mol) acetophenone, 5.31g (0.05mol) benzaldehyde, reaction temperature 140°C

[0041]

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Abstract

The invention relates a method of the synthesis of chalcone and derivatives thereof by using ionic liquid. Benzaldehyde and acetophenone are used as reactants and the molar ratio of the benzaldehyde and the acetophenone is 1:1 to 5:1; the ionic liquid is used as a catalyst and solvent and the mass of the ionic liquid added takes up 1:20 to 10:1 of the total mass of the reactants; the reaction pressure is normal pressure, the reaction temperature is 80 to 200 DEG C and the reaction time is 0.5 to 1.2 hours; the ionic liquid is composed of an alkyl imidazole cation or a pyridine cation functionalized by sulfonic group and inorganic or organic anions. The ionic liquid used by the invention is stable in the air and the water, is provided with an ignorable vapor pressure and is non volatile, which is an environment friendly catalyst and reaction solvent. The chalcone (or the derivatives of the invention ) of the reaction products of the ionic liquid can automatically be layered with the ionic liquid, which leads separation process to be easier and the ionic liquid can be used repeatedly by being dried in vacuum with the temperature of 110 DEG C for 1 to 6 hours after the reactions.

Description

technical field [0001] The invention relates to an organic synthesis method, in particular to a synthesis method for producing chalcones and derivatives thereof using ionic liquids as catalysts and solvent cleaning without using common organic solvents. Background technique [0002] Chalcones and their derivatives are products of cross-aldol condensation of aromatic aldehydes and ketones, which are widely used in insect attractants, UV protection, insect repellants, etc. They are important organic intermediates for the synthesis of various natural compounds, and they also have Important pharmacological effects, such as anti-cancer, anti-malarial, anti-cytotoxic, anti-inflammatory, anti-AIDS, etc. [0003] The method for synthesizing chalcone is a lot, common common method (such as US5179091, US6620842, WO2004056727 etc.) is to be reaction solvent with methanol or dehydrated alcohol, by substituted acetophenone and substituted benzaldehyde in alkali (NaOH, KOH, sodium alcohol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/796C07C49/84C07C45/74
CPCY02P20/54
Inventor 沈江汉王华刘中民孙颖刘红超
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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