Fast and green microwave-assisted conversion of essential oil allylbenzenes into the corresponding aldehydes via alkene isomerization and subsequent potassium permanganate promoted oxidative alkene group cleavage

Molecules. 2009 Sep 3;14(9):3411-24. doi: 10.3390/molecules14093411.

Abstract

Essential oil allylbenzenes from have been converted quickly and efficiently into the corresponding benzaldehydes in good yields by a two-step "green" reaction pathway based on a solventless alkene group isomerization by KF/Al(2)O(3) to form the corresponding 1-arylpropene and a subsequent solventless oxidation of the latter to the corresponding benzaldehyde by KMnO(4)/CuSO(4).5H(2)O. The assistance by microwave irradiation results in very short reaction times (<15 minutes). The green conversion of eugenol (4-allyl-2-methoxyphenol) into vanillin (4-hydroxy-3-methoxybenzaldehyde) has been carried out in a similar way, requiring however two additional microwave-assisted synthetic steps for acetylation of the hydroxy group prior to the oxidation reaction, and for the final deacetylation of vanillin acetate (4-acetoxy-3-methoxybenzaldehyde) by KF/Al(2)O(3) under solvent-free conditions, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Allyl Compounds / chemistry*
  • Benzaldehydes / chemistry*
  • Benzene Derivatives / chemistry*
  • Eugenol / chemistry
  • Green Chemistry Technology / methods*
  • Hydrolysis
  • Isomerism
  • Microwaves*
  • Oils, Volatile / chemistry*
  • Oxidation-Reduction
  • Potassium Permanganate / chemistry*
  • Solvents / chemistry

Substances

  • Alkenes
  • Allyl Compounds
  • Benzaldehydes
  • Benzene Derivatives
  • Oils, Volatile
  • Solvents
  • Potassium Permanganate
  • allylbenzene
  • Eugenol
  • vanillin