Synthesis of Novel Poly(ethyleneglycol)-400 Ionic Liquid and Its Application in Morita–Baylis–Hillman Reaction

Abstract

Novel Poly(ethyleneglycol)-400 ionic liquid containing imidazolium cations have been synthesized by the atom-efficient reaction of 1,2-dimethylimidazole with p-toluenesulfonate; the p-toluenesulfonate provides the anionic component of the resultant ionic liquid. It have been used for the first time as a new solvent for the Morita–Baylis–Hillman reaction under ambient conditions. A wide variety of aldehydes and active olefins participate very efficiently, resulting in good to excellent yields of products.

Keywords:

• 1,2-Dimethylimidazole
• ionic liquid
• Morita–Baylis–Hillman reaction
• p-toluenesulfonate
• synthesis

ACKNOWLEDGMENTS

We gratefully acknowledge financial support from the Xinzhou Teachers University Foundation ([2008] 79), the Higher School Science & Technology Development Project of Shanxi Province Education Department (No. 2010124), and the National Natural Science Foundation of China (No. 208020421B0211).

Notes

^a All reactions were performed with aldehydes (5 mmol) and activated alkenes (10 mmol) in a mixture of IL-400 and water (v/v, 1:1, 10 ml) in the presence of appropriate catalyst DABCO (5 mmol) at ambient temperature.

^b Refers to isolated, pure products after silica-gel chromatography.

^c The reaction was performed with benzaldehyde (5 mmol) and acrylonitrile (10 mmol) in 5 ml of IL-400 in the presence of appropriate catalyst DABCO (2.5 mmol) at ambient temperature.

^d The reaction was performed with benzaldehyde (5 mmol) and acrylonitrile (10 mmol) in 5 ml of IL-400 in the presence of appropriate catalyst DABCO (5 mmol) at ambient temperature.

^a All reactions were performed with benzaldehyde (5 mmol) and acrylonitrile (10 mmol) in a mixture of IL-400 and water (v/v, 1:1, 10 ml) in the presence of appropriate catalyst DABCO (5 mmol) at ambient temperature.