Synlett, Table of Contents Synlett 2015; 26(09): 1263-1268DOI: 10.1055/s-0034-1380503 letter © Georg Thieme Verlag Stuttgart · New York Environmentally Sustainable Magnetic Solid Sulfonic Acid: An Efficient and Reusable Catalyst for the Pechmann Reaction Akbar Mobaraki Department of Chemistry, K. N. Toosi University of Technology, P.O. Box 16315-1618, Tehran, Iran Email: bmovass1178@yahoo.com , Shahriar Yasham Department of Chemistry, K. N. Toosi University of Technology, P.O. Box 16315-1618, Tehran, Iran Email: bmovass1178@yahoo.com , Barahman Movassagh* Department of Chemistry, K. N. Toosi University of Technology, P.O. Box 16315-1618, Tehran, Iran Email: bmovass1178@yahoo.com › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract An environmentally benign sulfonic acid nanocomposite based on Fe3O4@SiO2 core–shell magnetic nanoparticles, Fe3O4@SiO2@Et-PhSO3H, was prepared and the acidity and utility of the catalyst were explored for the synthesis of a diverse range of coumarin derivatives under solvent-free conditions. The catalyst shows potential for scale up in the synthesis of coumarins with high purity and was easily separated by using an external magnet. The recovered catalyst was reused in seven cycles without any significant loss of activity. Key words Key wordsPechmann condensation - coumarin - magnetic particles - nanocomposites - sulfonic acid Full Text References References and Notes 1 Melero JA, van Grieken R, Morales G. Chem. Rev. 2006; 106: 3790 2 Ertl G, Knozinger H, Schuth F, Weitkamp J. Handbook of Heterogeneous Catalysis . 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A: Chem. 2004; 209: 117 33 General Synthesis of Coumarins by Pechmann Reaction: A mixture of phenol (2 mmol), β-keto ester (2 mmol), and catalyst (0.3 mol%) was heated and magnetically stirred at 120 °C for the appropriate time under solvent-free conditions (Table 4). In many cases, the coumarins separated out as a solid mass on the inner wall of the flask at the end of the reaction. Upon completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature, hot EtOH (5 mL) was added, and the mixture was stirred for 15 min. The catalyst was removed from the reaction mixture by magnetic separation. The ethanolic solution was evaporated, the residue was poured onto crushed ice, and the resulting crude product was filtered off and recrystallized from ethanol to afford pure coumarin. Supplementary Material Supplementary Material Supporting Information
