Russian Journal of Organic Chemistry

, Volume 45, Issue 6, pp 810–814 | Cite as

Synthesis and some transformations of (−)-carveol

  • R. F. Valeev
  • N. S. Vostrikov
  • M. S. Miftakhov


Reduction of the oxo group in (−)-carvone with LiAlH4, NaBH4, and (i-Bu)2AlH was performed. It was found that the reduction with the system CeCl3 · 7 H2O-NaBH4 in methanol at 20°C is the most practical procedure for the synthesis of (−)-carveol. Solvolysis of (−)-carvyl methanesulfonate gave products of SN2 and SN2′ replacement of the methylsulfonyloxy group, the latter slightly prevailing. Overman rearrangement of (−)-carveol resulted in the formation of the corresponding trichloroacetamide derivative, and intramolecular iodoetherification of the title compound afforded 6-iodomethyl-2,6-dimethyl-7-oxabicyclo[3.2.1]oct-2-ene.


Petroleum Ether Solvolysis Carvone Carveol Methanesulfonyl Chloride 
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Copyright information

© Pleiades Publishing, Ltd. 2009

Authors and Affiliations

  • R. F. Valeev
    • 1
  • N. S. Vostrikov
    • 1
  • M. S. Miftakhov
    • 1
  1. 1.Institute of Organic Chemistry, Ufa Research CenterRussian Academy of SciencesUfaRussia

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