Hydrochloric Acid → HCID 19068250, compound

Participants

Reaction Steps

1.44 g (48 mmol) of sodium hydride (80% in oil) and 25 ml of DMF were introduced into a three-necked flask under a stream of nitrogen. A solution of 6.73 g (40 mmol) of methyl 4-mercaptobenzoate in 60 ml of DMF was added dropwise and the mixture was stirred until the evolution of gas had ceased. A solution of 16.1 g (48 mmol) of 3-(1-adamantyl)-4-methoxybenzyl bromide in 90 ml of DMF was then added and the mixture was stirred at room temperature for eight hours. The reaction medium was poured into water, acidified to pH 1 with hydrochloric acid and extracted with ethyl ether. The organic phase was separated out after settling had taken place, washed with water, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a column of silica eluted with a mixture of dichloromethane and hexane (40/60). After evaporation of the solvents, 16.75 g (99%) of the expected methyl ester, having a melting point of 143°-5° C., were recovered.

Provenance & Evidence