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The solvent effect in β-pinene oxide rearrangement

Abstract

Perillyl alcohol preparation by the rearrangement of β-pinene oxide was studied. Sn-MCM-41, USY and FeCl3 were used as catalysts. The solvent influence was tested using basic polar solvents—dioxane, acetonitrile, DMF, DMA, DMSO and N-methyl pyrrolidone. It was found that the solvent has significant influence on the selectivity: Sn-MCM-41 was in previous works used for β-pinene oxide rearrangement for the preparation of myrtenal or myrtenol in acetonitrile or nitromethane as solvent. When DMSO was used, a high yield of perillyl alcohol was obtained. The highest selectivity to perillyl alcohol (66 %) was obtained when Sn-MCM-41 was used as a catalyst under the following conditions: 70 °C, 10 wt% of catalyst, volume ratio β-pinene oxide : solvent = 1:8. The selectivity may be slightly increased by decrease of ratio β-pinene oxide : solvent in the case of Sn-MCM-41. Moreover, Sn-MCM-41 may be reused at least four times without any loss of selectivity or activity.

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Correspondence to Eliška Vyskočilová.

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Vyskočilová, E., Malý, M., Aho, A. et al. The solvent effect in β-pinene oxide rearrangement. Reac Kinet Mech Cat 118, 235–246 (2016). https://doi.org/10.1007/s11144-016-0994-9

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Keywords

  • Sn-MCM-41
  • Perillyl alcohol
  • β-Pinene oxide
  • Solvent effect