2,2-Dimethoxypropane → Benzoic Acid

Participants

Reaction Steps

Acetone (5.6 ml) and dimethoxypropane (5.6 ml) were added to 4-(2-(α-D-mannopyranosyloxy) phenyl)benzoic acid (0.54 g, 1.43 mmol) to form a heterogeneous mixture. A catalytic amount of p-toluenesulfonic acid monohydrate was introduced and the reaction was stirred at room temperature for 45 minutes, at which point a clear, homogeneous solution was obtained. The solvent was removed in vacuo and the yellow oily residue taken up in ethyl acetate, washed with saturated sodium bicarbonate then saturated sodium chloride, dried (MgSO4) and concentrated in vacuo to afford 4-(2-(2,3:4,6-di-O-isopropylidene)α-D-mannopyranosyloxy)phenyl)benzoic acid (0.70 g).

Provenance & Evidence