Prins cyclization for the preparation of 2-isobutyl-4-methyl-tetrahydro-2H-pyran-4-ol using supported heteropoly acids

Prins cyclization for the preparation of 2-isobutyl-4-methyl-tetrahydro-2H-pyran-4-ol using... The selective preparation of 2-isobutyl-4-methyl-tetrahydro-2H-pyran-4-ol (also called Florosa or Florol) was performed. Prins cyclization of isoprenol and isovaleraldehyde was used for the preparation of this important fragrant compound. Heteropoly acids (phosphotungstic and phosphomolybdic) were used as a catalyst in homogeneous and also in heterogeneous arrangements (after their immobilization). The only solvent necessary for the reaction was water that enables the increase of the selectivity to the desired product by hydrolysis of catalyst-carbocation intermediates. In a flow, both heteropoly acids were successfully anchored on siliceous MCM-41 and resultant materials were characterized by XRF, XRD, SEM, FTIR, UV–Vis, and nitrogen adsorption. Heterogenization was performed in water as a solvent. Anchored heteropoly acids were used in Prins cyclization under the same conditions (addition of water), and the selectivity was even higher (96 %), comparing the homogeneous arrangement. No leaching of catalyst from solid was observed. Moreover, the catalyst may be reused without loss of activity and selectivity at least four times. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Prins cyclization for the preparation of 2-isobutyl-4-methyl-tetrahydro-2H-pyran-4-ol using supported heteropoly acids

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Publisher
Springer Netherlands
Copyright
Copyright © 2016 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-016-2511-1
Publisher site
See Article on Publisher Site

Abstract

The selective preparation of 2-isobutyl-4-methyl-tetrahydro-2H-pyran-4-ol (also called Florosa or Florol) was performed. Prins cyclization of isoprenol and isovaleraldehyde was used for the preparation of this important fragrant compound. Heteropoly acids (phosphotungstic and phosphomolybdic) were used as a catalyst in homogeneous and also in heterogeneous arrangements (after their immobilization). The only solvent necessary for the reaction was water that enables the increase of the selectivity to the desired product by hydrolysis of catalyst-carbocation intermediates. In a flow, both heteropoly acids were successfully anchored on siliceous MCM-41 and resultant materials were characterized by XRF, XRD, SEM, FTIR, UV–Vis, and nitrogen adsorption. Heterogenization was performed in water as a solvent. Anchored heteropoly acids were used in Prins cyclization under the same conditions (addition of water), and the selectivity was even higher (96 %), comparing the homogeneous arrangement. No leaching of catalyst from solid was observed. Moreover, the catalyst may be reused without loss of activity and selectivity at least four times.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Mar 24, 2016

References

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