Pechmann reaction in non-chloroaluminate acidic ionic liquids under solvent-free conditions

Abstract

Four non-chloroaluminate acidic ionic liquids have been used as catalysts for Pechmann condensations of phenols under solvent-free conditions. SO 3H-functionalized trifluoromethanesulfonate imidazolium ionic liquid has proved to be the most active catalyst. Ionic liquid loads as low as 5 mol % can be used leading to high yields with activated phenols at an oil bath temperature of 80°C. The acidities of the four ionic liquids have also been tested using the Hammett method in dichloromethane. The results are consistent with their catalytic activities as observed in the Pechmann reaction of resorcinol. This methodology offers significant improvements for the synthesis of coumarins with regard to yield of products, simplicity in operation, and green aspects by avoiding toxic catalysts and solvents. © 2005 WILEY-VCH Verlag GmbH & Co. KGaA.