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β-Cyclodextrin and its derivatives mediate selectivity in reduction of (R)-(+)-pulegone with sodium dithionite

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Abstract

Pulegone is reduced in two stages by sodium dithionite—first to menthone and later to epimeric methols. The presence ofβ-cyclodextrin (BCD) and its derivatives resulted in more of the alcohols being formed. While the double bond was reduced predominantly in water, the ketone moiety was also reduced in a water-DMF mixture. A small percentage of menthone remained relatively unaffected in water-DMF even in the presence of BCD and its derivatives. Although no unreacted pulegone could be detected, exclusive alcohol formation was also not observed. Reduction of the double bond was found to be faster than that of the ketone.

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Authors and Affiliations

  1. Plantation Products and Flavour Technology, Central Food Technological Research Institute, 570 013, Mysore, India

    Ramaswamy Ravichandran & Soundar Divakar

Authors
  1. Ramaswamy Ravichandran
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  2. Soundar Divakar
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Ravichandran, R., Divakar, S. β-Cyclodextrin and its derivatives mediate selectivity in reduction of (R)-(+)-pulegone with sodium dithionite. J Incl Phenom Macrocycl Chem 18, 369–375 (1994). https://doi.org/10.1007/BF00707385

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  • DOI: https://doi.org/10.1007/BF00707385

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