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Practical and efficient synthesis of tetrahydrobenzo[b]pyran using caffeine supported on silica as an ionic liquid solid acid catalyst

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Abstract

The new catalyst silica-caffeine hydrogen sulfate [SiO2-caff.]HSO4 was conveniently prepared from commercially available 3-chloropropyltriethoxysilane via immobilization on silica followed by reaction with caffeine. The catalyst prepared was then characterized by the FT-IR spectroscopy, TGA, EDX, and SEM techniques. It was found that this heterogeneous catalyst was a highly efficient one for the synthesis of tetrahydrobenzo[b]pyrans in good-to-high yields, and could be recovered by a simple filtration of the reaction solution and reused for five consecutive runs. The attractive features of this method are simple procedure, clean reaction, easy work-up, use of a reusable catalyst, and performing a multi-component reaction.

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Acknowledgements

We gratefully acknowledge the financial support of the Research Council of the Shahrood University of Technology.

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Authors and Affiliations

  1. School of Chemistry, Shahrood University of Technology, Shahrood, 3619995161, Iran

    Mohammad Bakherad, Ali Keivanloo, Elmira Moradian, Amir H. Amin & Rahele Doosti

  2. Chemistry Department, Science and Research Branch, Islamic Azad University, Tehran, Iran

    Mahsa Armaghan

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  1. Mohammad Bakherad
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  2. Ali Keivanloo
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  3. Elmira Moradian
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  4. Amir H. Amin
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  5. Rahele Doosti
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Correspondence to Mohammad Bakherad.

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Bakherad, M., Keivanloo, A., Moradian, E. et al. Practical and efficient synthesis of tetrahydrobenzo[b]pyran using caffeine supported on silica as an ionic liquid solid acid catalyst. J IRAN CHEM SOC 15, 2811–2819 (2018). https://doi.org/10.1007/s13738-018-1468-y

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