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Contribution to elucidation of the mechanism of preparation of 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol

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Abstract

The effects of catalyst type (sulfuric acid, Amberlyst 15, p-toluenesulfonic acid, and p-dodecylbenzenesulfonic acid) and of addition of water on the preparation of 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol by Prins cyclization were studied. It was discovered that in the absence of added water the amphiphilic character of the acid had the main effect and that organic acids were unsuitable for preparation of this compound. From the perspective of the ratio of the amount of the desired product to that of dihydropyrans, after addition of water the results obtained by use of p-toluenesulfonic acid (ratio 3.5, selectivity 67 %) were comparable with those obtained by use of sulfuric acid and were better than those obtained by use of Amberlyst 15 (ratio 2.3, selectivity 68 %). A detailed study of the mechanism confirmed that addition of water to the double bonds of dihydropyrans does not occur.

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Authors and Affiliations

  1. Department of Organic Technology, University of Chemistry and Technology Prague, Technicka 5, Prague 6, 166 28, Czech Republic

    Eliška Vyskočilová, Lucie Rezková, Eva Vrbková, Iva Paterová & Libor Červený

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  1. Eliška Vyskočilová
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  2. Lucie Rezková
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  3. Eva Vrbková
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  4. Iva Paterová
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  5. Libor Červený
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Correspondence to Eliška Vyskočilová.

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Vyskočilová, E., Rezková, L., Vrbková, E. et al. Contribution to elucidation of the mechanism of preparation of 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol. Res Chem Intermed 42, 725–733 (2016). https://doi.org/10.1007/s11164-015-2052-z

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  • DOI: https://doi.org/10.1007/s11164-015-2052-z

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