1-Butanol → 4-Butoxymethyl-benzonitrile

Participants

Reaction Steps

To a mixture of NaH (270 mg/66% in oil) and THF (20 mL) was added n-butanol (1.1 mL) at 0° C., which was stirred for 45 minutes at room temperature. The reaction mixture was cooled to 0° C., and a mixture of 4-cyanobenzyl bromide (1.5 g) and THF (10 mL) was added by drops thereto at the same temperature. The reaction mixture was stirred for 3 hours at room temperature, after which DMF (10 mL) was added to the reaction mixture, which was stirred for 4.5 hours at the same temperature. Water was added to the reaction mixture, which was then extracted with diethyl ether. The organic layer was washed with saturated brine, after which the solvent was evaporated from the organic layer under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:6) to obtain the titled compound (1.2 g).

Provenance & Evidence