Synthesis of 4-hydroxy-2,5-dimethylfuran-3(2H)-one (furaneol) from (2R,3R)-tartaric acid

Abstract

(2R,3R)-Tartaric acid (6) has been converted through a five-step sequence into the important volatile flavour and aroma component 4-hydroxy-2,5-dimethylfuran-3(2H)-one (furaneol)(1) in 18.5% overall yield. The key step involves the formation of (4R,5R)-4,5-diacetyl-2,2-dimethyl-1,3-dioxolane (10) by reaction of methylmagnesium chloride with the corresponding 4,5-bis(dimethylamide). The same dioxolane (10) was also prepared via a related reaction sequence involving a Grignard type reaction on the corresponding dinitrile.