Acetic Acid → 2-[p-(Benzyloxy)phenoxy]propionaldehyde

Participants

Reaction Conditions

Reaction Steps

A 1.5 molar solution of diisobutylaluminum hydride in toluene (138 mL, 0.207 mol) is added dropwise to a mixture of methyl 2-[p-(benzyloxy)phenoxy]propionate (56.4 g, 0.197 mol) in toluene at -65° C. under a nitrogen atmosphere. The reaction mixture is stirred at -65° C. for 5 hours. Acetic acid (70 mL) is added dropwise and the reaction mixture is warmed to room temperature, diluted with hexanes, washed with 10% hydrochloric acid solution and water, dried and concentrated in vacuo to obtain an oil. Flash chromatography of the oil using silica gel and eluting with a 1:1 methylene chloride/hexanes solution gives the title product as a white solid (21.44 g, mp 50°-51° C.).

Provenance & Evidence