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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 (CC BY 3.0).

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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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