2-Acetoxymethyl-4-benzyloxybut-1-yl acetate → 1,4-Butanediol, 2-[(acetyloxy)methyl]-, 1-acetate

Participants

Reaction Steps

To a solution of 2-acetoxymethyl-4-benzyloxy-but-1-yl acetate (55 g, 0.187 mol) in ethanol (250 ml) was added 10% palladium on carbon (2.5 g), and the mixture hydrogenated at atmospheric pressure and room temperature. When the theoretical hydrogen uptake had been achieved (18 hours), the reaction was stopped and filtered through Celite. Evaporation of the filtrate gave a colourless oil (35 g). This was purified by column chromatography on silica gel, elution with 2% methanol in chloroform affording 2-acetoxy-methyl-4-hydroxybut-1-yl acetate as a clear oil (32.9, 86%). δH (CDCl3) 1.61 (2H, q, CHCH2CH2), 2.04 (6H, s, 2×OCOCH3), 2.20 (1H, m, CH), 2.61 (1H, br s, D2O exchangeable, OH), 3.68 (2H, t, CH2OH), 4.04 (4H, d, 2×CH2OCOCH3).

Provenance & Evidence