Benzyl Alcohol → HCID 18184950, compound

Participants

Reaction Steps

A mixture of sodium hydride (5.24 g, 55% dispersion in mineral oil), benzyl alcohol (13 g) and anhydrous N,N-dimethylformamide (150 ml) was stirred at room temperature for 30 minutes. To this mixture was added t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate (8.7 g) at room temperature and this mixture was stirred for 18 hours. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on a silica gel column using hexane: ethyl acetate=10:1 as the eluant to afford the title compound (29.2 g, yellow crystals, mp 108-110° C.).

Provenance & Evidence