4-Hydroxybenzyl Alcohol → 4-(Quinolin-2-ylmethoxy)benzyl alcohol

Participants

Reaction Steps

A solution of 4-hydroxybenzyl alcohol (14.46 g) in dry dimethylformamide (100 ml) was added dropwise to a stirred suspension of sodium hydride (60% dispersion in oil, 5.6 g), (washed with petroleum spirit 40°-60° C.) in dry dimethylformamide (50 ml) cooled under an atmosphere of nitrogen at 0°-5° C. The mixture was stirred at room temperature for 0.5 hour then re-cooled to 0°-5° C. and a solution of 2-chloromethylquinoline (20.69 g) in dry dimethylformamide (100 ml) added dropwise. The mixture was stirred overnight at room temperature, concentrated in vacuo and diluted with water. The crude product was obtained after cooling and filtration.

Provenance & Evidence