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.