Microwave-assisted intermolecular aldol condensation: Efficient one-step synthesis of 3-acetyl isocoumarin and optimization of different reaction conditions

Abstract

This paper describes the optimization and comparison of conventional and microwave-assisted methods for efficient, cheap, one-pot, and straightforward synthesis of isocoumarins under mild reaction conditions. On this basis of this aim, synthesis of 3-acetyl isocoumarin from 2-formylbenzoic acid with mono-chloroacetone was chosen as a model reaction. Afterward, four different methods conventional (Method A), microwave open vessel (Method B), microwave sealed vessel (Method C), and microwave closed system (Method D) were used methodologically to determine best experimental conditions for each of these methods in this model reaction. The results revealed that developed Methods A, C and D could be used successfully under solvent-free conditions with good yields (84-87%) for the future efficient, one-pot synthesis of isocoumarins. This paper is also a first for characterizing 3-acetyl isocoumarin by using ATR, H-1 NMR, C-13 NMR and GC-MS. (C) 2015 The Authors. Production and hosting by Elsevier B.V. on behalf of King Saud University.