Benzylsulfonic acid functionalized mesoporous Zr-TMS catalysts: An efficient and recyclable catalyst for the preparation of coumarin derivatives by Pechmann condensation reaction |
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| Affiliation: | 1. Key Laboratory of Pulp and Paper Science & Technology of Ministry of Education, State Key Laboratory of Biobased Material and Green Papermaking, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, PR China;2. Key Laboratory of Processing and Testing Technology of Glass & Functional Ceramics of Shandong Province, School of materials Science and Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, PR China;3. State Key Laboratory of Crystal Materials, Institute of Crystal Materials, Shandong University, Jinan 250100, PR China |
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| Abstract: | Benzylsulfonic acid functionalized mesoporous Zr-TMS (Zr-TMS-BSA, Zr-TMS, zirconia based transition metal oxide mesoporous molecular sieves) catalyst is used as an alternative to conventional acid catalysts in the von Pechmann condensation of aromatic alcohols with ethyl acetoacetate leading to the formation of coumarin derivatives in solvent free condition at 150 °C. Three types of coumarins, 7-hydroxy-4-methylcoumarin (β-methylumbelliferone), 7-methoxy-4-methylcoumarin (Methyl-4-methylumbelliferyl ether) and 7,8-benzo-4-methylcoumarin derivatives have been prepared using resorcinol, 3-methoxyphenol and 1-naphthol, respectively. The catalytic activity and the recycle studies of the catalyst in all the three reactions proved the superior performance of the catalyst. Further the products were confirmed by GC, elemental analysis, melting point and NMR techniques. Finally, the probable mechanism for Pechmann condensation using Zr-TMS-BSA catalyst has been reported. |
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