Organic Reactions in Ionic Liquids: Knoevenagel Condensation Catalyzed by Ethylenediammonium Diacetate

Ce Su; Zhen-Chu Chen; Qin-Guo Zheng

doi:10.1055/s-2003-37643

PAPER

Organic Reactions in Ionic Liquids: Knoevenagel Condensation Catalyzed by Ethylenediammonium Diacetate

Ce Su^b, Zhen-Chu Chen*^a,b, Qin-Guo Zheng^c
^a Ningbo Institute of Technology, Zhejiang University, Ningbo, 315104, P. R. China
^b Department of Chemistry, Zhejiang University (Xi-xi campus), Hangzhou, 310028, P. R. China
e-Mail: zhenchuc@mail.hz.zj.cn;
^c Pharmaceutical Sciences Research Institute, Aston University, Aston Triangle, Birmingham B4 7ET, UK

Abstract

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Abstract

The moisture and air stable ionic liquids 1-butyl-3-methylimidazonium tetrafluoroborate [bmim]BF₄ and 1-butyl-3-methylimidazonium hexafluorophosphate [bmim]PF₆ were used as ‘green’ recyclable alternatives to volatile organic solvents (VOCs) for ethylenediammonium diacetate (EDDA) catalyzed Knoevenagel condensation between aldehydes or ketones with active methylene compounds. Both aldehydes and ketones gave satisfactory results. The ionic liquids containing catalyst EDDA were recycled several times with no decreases in yields and reaction rates. In the case of 2-hydroxybenzaldehyde, the reactions led to the formation of 3-substituted coumarins under standard reaction conditions.

Key words

ionic liquid - condensation - ketones - aldehydes - Knoevenagel reaction - active methylene compounds

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