Methyl chloroformate → HCID 12085579, compound

Participants

Reaction Steps

To a solution of 4-allyloxy-2′-hydroxybenzophenone (0.87 g) in tetrahydrofuran (14 mL) was added triethylamine (0.53 mL) and methyl chloroformate (0.29 mL) at 0° C. After warming to room temperature, the mixture was stirred for 1.5 hours. Insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure. To a solution of the residue in tetrahydrofuran (18 mL) and water (9 mL) was added sodium borohydride (0.52 g) at 0° C. After warming to room temperature, and the mixture was stirred for 2.5 hours. To the reaction mixture was added 0.5 mol/L hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=8/1) to give 2-(4-allyloxybenzyl)phenol (0.72 g).

Provenance & Evidence