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Molecules 2009, 14(9), 3411-3424; doi:10.3390/molecules14093411
Article

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

1
, 2
, 2
 and 1,*
1 Department of Science, Systems, and Models, Roskilde University, P.O. Box 260, DK-4000, Roskilde, Denmark 2 Department of Organic Chemistry, University of Science, National University of Ho Chi Minh City, 227 Nguyen Van Cu, Ho Chi Minh City, Vietnam
* Author to whom correspondence should be addressed.
Received: 12 August 2009 / Revised: 2 September 2009 / Accepted: 2 September 2009 / Published: 3 September 2009
(This article belongs to the Special Issue Microwave Assisted Synthesis)
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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/Al2O3 to form the corresponding 1-arylpropene and a subsequent solventless oxidation of the latter to the corresponding benzaldehyde by KMnO4/CuSO4·5H2O. 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/Al2O3 under solvent-free conditions, respectively.
Keywords: microwave irradiation; solvent-free reaction; alkene isomerization; alkene oxidation microwave irradiation; solvent-free reaction; alkene isomerization; alkene oxidation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Luu, T.X.T.; Lam, T.T.; Le, T.N.; Duus, F. 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, 14, 3411-3424.

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