Microwave-Assisted Mild Conversion of Natural Dihydrotagetone into 5-Isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone, an Analogue of Whisky Lactone*

Arun K. Sinha; Bhupendra P. Joshi; Anuj Sharma; Vinod Kumar; Ruchi Acharya

doi:10.1071/CH06380

RESEARCH ARTICLE

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Microwave-Assisted Mild Conversion of Natural Dihydrotagetone into 5-Isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone, an Analogue of Whisky Lactone*

Arun K. Sinha ^A ^B , Bhupendra P. Joshi ^A , Anuj Sharma ^A , Vinod Kumar ^A and Ruchi Acharya ^A

+ Author Affiliations

- Author Affiliations

^A Natural Plant Products Division, Institute of Himalayan Bioresource Technology, Palampur H.P. 176061, India.

^B Corresponding author. Email: aksinha8@rediffmail.com

Australian Journal of Chemistry 60(2) 124-127 https://doi.org/10.1071/CH06380
Submitted: 17 October 2006 Accepted: 7 December 2006 Published: 13 February 2007

Abstract

A microwave-assisted mild protocol is developed for the synthesis of 5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone, an analogue of whisky lactone, from dihydrotagetone, an acyclic monoterpenoid obtained from Tagetes minuta. The methodology involved oxidation of dihydrotagetone in the presence of sodium metaperiodate/potassium permanganate/alumina to give 2,6-dimethyl-4-oxo-heptanoic acid, which upon reduction and subsequent lactonization provided 5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone. The reaction is also conducted under conventional conditions and is compared with the microwave method.

Acknowledgments

B.P.J. and A.S. are indebted to CSIR, and V.K. thanks UGC, Delhi, for the award of SRF. The authors gratefully acknowledge the Director of the Institute of Himalayan Bioresource Technology, Palampur, for kind cooperation and encouragement.

References

^* IHBT communication no. 0539

^A Flavor-Extract Manufacturer Association; Generally Regarded As Safe.

Microwave-Assisted Mild Conversion of Natural Dihydrotagetone into 5-Isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone, an Analogue of Whisky Lactone*

Abstract

Acknowledgments

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