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Citation: GONG Kai, FANG Dong, SHI Qun-Rong, LIU Zu-Liang. Knoevenagel Condensation Reaction Catalyzed by Functionalized Ionic Liquid[J]. Chinese Journal of Applied Chemistry, ;2007, 24(9): 1089-1091. shu

Knoevenagel Condensation Reaction Catalyzed by Functionalized Ionic Liquid

1.
School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing 210094

Corresponding author: LIU Zu-Liang,
Received Date: 8 September 2006
Available Online: 30 January 2007

The basic functionalized ionic liquid, 1-butyl-3-methylimidazolium hydroxide([BMIM]OH), was prepared and used to catalyze the Knoevenagel condensation of aromatic aldehydes with malononitrile or ethyl cyanoacetate. The results show that the Knoevenagel condensation proceeds smoothly in the presence of 5% basic functionalized ionic liquid to afford the desired alkenes in good purity and 81%~97% yields under relatively mild conditions without solvent or any added catalyst. In this catalyst system, the Knoevenagel condensations of a series of aromatic aldehydes with malononitrile or ethyl cyanoacetate were programmed and a mechanism was postulated as well. When aromatic aldehydes reacted with ethyl cyanoacetate, the corresponding alkenes proved to be E-isomers by ¹H NMR. The procedure is simple and the ionic liquid could be recycled efficiently. With the condensation of benzaldehyde and malononitrile as an example, the ionic liquid was recycled three times with a slight decrease in catalytic activity and a yield of 86% was gained.
- basic functionalized ionic liquid,
- catalyze,
- Knoevenagel condensation,
- malononitrile,
- ethyl cyanoacetate
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