THE C- AND O-BENZYLATION OF L-ASCORBIC ACID

Abstract

Alkylation of sodium L-ascorbate with benzyl chloride yielded a 2-C-benzyl-3-keto-hexulo-sonic acid lactone and 3-O-benzyl-L-ascorbic acid, the yield of each being dependent on reaction conditions. Other products obtained from the alkylations were 2,3-di-O-benzyl-L-ascorbic acid and a 1-deoxy-1-C-phenyl-2-hexulose. Treatment of 3-O-methyl-5,6-O-iso-propylidene-L-ascorbic acid with benzyl chloride and sodium methoxide yielded the 2-O-benzyl derivative.