Knoevenagel Condensation Catalyzed by Ethylenediammonium Diacetate (original) (raw)

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

Ce Su, Zhen-Chu Chen*, Qin-Guo Zheng

*Department of Chemistry, Zhejiang University (Xi-xi campus), Hangzhou, 310028, P. R. China, Email: zhenchucmail.hz.zj.cn

C. Su, Z.-C. Chen, Q.-G. Zhen, Synthesis, 2003, 555-559.

DOI: 10.1055/s-2003-37643

Abstract

The ionic liquid 1-butyl-3-methylimidazonium tetrafluoroborate [bmim]BF4was used for ethylenediammonium diacetate (EDDA)-catalyzed Knoevenagel condensation between aldehydes or ketones with active methylene compounds. Catalyst and solvent can be recycled.

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Details

The document explores the use of ionic liquids, specifically 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4) and 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim]PF6), as green solvents for the Knoevenagel condensation reaction. This reaction, catalyzed by ethylenediammonium diacetate (EDDA), involves the condensation of aldehydes or ketones with active methylene compounds to form electrophilic olefins. The study highlights the benefits of using ionic liquids over traditional volatile organic solvents, such as their stability, recyclability, and ability to accelerate reactions while providing high yields. The research demonstrated that both fresh and recycled ionic liquids maintained high efficiency and yield in the condensation reactions. The document also compares the performance of ionic liquids with traditional solvents, showing that ionic liquids offer faster reaction times and higher yields. Additionally, the scope of the reaction was expanded to various aldehydes and ketones, all yielding excellent results. The study concludes that using ionic liquids for the Knoevenagel condensation is an environmentally friendly, efficient, and high-yielding method, with the added benefit of being able to recycle the ionic liquids and catalyst. This method provides a simple and effective approach for synthesizing electrophilic alkenes.

Key Words

Ionic liquids, Green Chemistry, Catalysis, Knoevenagel Condensation, Carbonyl Compounds,Coumarins

ID: J66-Y2003-1790