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Communication | Special issue | Vol 7, No. 1, 1977, pp.57-60
Published online, 1st January, 1970
DOI: 10.3987/S-1977-01-0057
The Birch Reduction of Quercetin Methayl Ethers

James G. Sweeny, Terence Radford, and Guillermo A. Iacobucci*

*Corporate Research and Development, The Coca-Cola Company, P. O. Drawer 1734, Atlanta, GA 30301, U.S.A.

Abstract

The sodium-ammonia reduction of 3,3’,4’,5,7-pentamethylquercetin (I) afforded the dihydrochalcone (II) in 54% yield. In contrast, the reduction of 3’,4’,5,7-tetramethylquercetin (III) yielded the α-hydroxydihydrochalcone (IV) (64% yield) as major product. The reactions are believed to proceed through the intermediary formation of 2,3-trans-dihydroquercetins.