(4S)-4-[(Hexadecyloxy)methyl]-2,2-dimethyl-1,3-dioxolane → (2R)-3-(Hexadecyloxy)-1,2-propanediol

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Reaction Steps

A stirred mixture of 28 g of (S)-4-[(hexadecyloxy)methyl]-2,2-dimethyl-1,3-dioxolane in 190 ml of methyl alcohol and 21 ml of 1N hydrochloric acid is refluxed for 2 hours followed by cooling in an ice bath. The resulting solid is filtered and washed with cold acetone. The solid is crystallized from acetone to give 18.2 g of crystals which liquified at ambient temperature. The resulting oil is purified by chromatography on silica gel using 1:1 ethyl acetate:hexanes. Fractions containing product are combined and evaporated to a material which is stirred with acetone at -20° C. to give 4.1 g of crystalline solid, m.p. 65°-66° C.

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