Acetone → 3-(Benzyloxy)-1,2-propanediol

Participants

Reaction Steps

Into a mixed solution of acetone (800 ml) and glycerin (199 g, 2.16 mol) was added 98% sulfuric acid (6.9 g) at about 25° C., and the mixture was stirred for 3 hours. To this reaction solution was added triethylamine (18.0 g), and the solvent was distilled off under reduced pressure. Into a solution prepared by suspending sodium hydroxide (98.5 g) in toluene (526 ml) was dropped the above-described concentration residue at 55 to 75° C. Into this reaction solution, benzyl chloride (229 g, 1.81 mol) was dropped at 95 to 105%, and the mixture was reacted for 5 hours while distilling components of lower boiling points off. After completion of the reaction, water (366 ml) was added, and the liquid was partitioned. To the resultant toluene layer was added 98% sulfuric acid (22.9 g) and water (571 ml), and the mixture was stirred at about 50° C. for 5 hours stirred, then, the toluene layer was concentrated under reduced pressure. To the residue was added heptane (267 ml), methanol (534 ml) and water (267 ml), and the mixture was liquid-partitioned. The aqueous layer was liquid-partitioned by further adding heptane (267 ml), and the resulting aqueous layer was concentrated under reduced pressure to remove methanol. To the concentrated liquid was added sodium chloride (46 g), and the mixture was extracted twice with ethyl acetate (267 ml). The resultant ethyl acetate solution was concentrated under reduced pressure to obtain a title compound (277 g, yield 84%).

Provenance & Evidence