One-step microwave-assisted asymmetric cyclisation/hydrogenation of citronellal to menthols using supported nanoparticles on mesoporous materials

Org Biomol Chem. 2010 Jun 21;8(12):2845-9. doi: 10.1039/c003600e. Epub 2010 Apr 29.

Abstract

The selective conversion of citronellal to menthols, with good diastereoselectivities to (-)-menthol for the case of (+)-citronellal as starting material, can effectively be carried out in a one-step reaction under microwave irradiation catalysed by supported nanoparticles on mesoporous materials. 2% Pt/Ga-MCM-41 was found to be the optimum catalyst for the reaction, with a quantitative conversion of starting material and selectivities above 85% to menthols obtained in short reaction times (typically 15 min). These results constitute the first report of a simple microwave-assisted one-step cyclisation/hydrogenation process for the production of menthols.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acyclic Monoterpenes
  • Aldehydes / chemistry*
  • Cyclization
  • Hydrogenation
  • Menthol / chemistry*
  • Microwaves*
  • Monoterpenes / chemistry*
  • Nanoparticles / chemistry*
  • Stereoisomerism

Substances

  • Acyclic Monoterpenes
  • Aldehydes
  • Monoterpenes
  • Menthol
  • citronellal