Benzyl Alcohol → HCID 54031137, compound

Participants

Reaction Steps

To a solution of 3.0 g (6.7 mmol) of 3-acetyloxy-5-(octadecyloxy)benzenecarboxylic acid in 70 ml of dry toluene and 10 ml of dry DMF cooled in an ice bath was added 1.7 ml (8 mmol) of diphenylphosphoryl azide followed by 1.1 ml (8 mmol) of triethylamine. The reaction mixture was stirred in the ice bath for 1.5 hours and then was heated at 90° for 5 hours. Benzyl alcohol (20 ml) was added and heating at 90° was continued for 16 hours. The solvents were removed at reduced pressure and ethyl acetate was added to the residue. The extract was washed with NaHCO3 solution and then cooled at -18°. The precipitate was removed by filtration and the filtrate was concentrated at reduced pressure to an oil which was purified by chromatography on 150 g of silica gel using 25% ethyl acetate-hexane to give 1.87 g (50% yield, mp 57°-59 °) of 3-acetyloxy-5-(octadecyloxy)phenylcarbamic acid phenylmethyl ester.

Provenance & Evidence