Water → 4-Benzyloxy-3-ethyl-5-methyl-benzonitrile

Participants

Reaction Conditions

Reaction Steps

3-Ethyl-4-hydroxy-5-methyl-benzonitrile (6.0 g, 37 mmol) is dissolved in acetonitrile (80 mL) and K2CO3 (10.1 g, 73 mmol) and benzyl bromide (6.56 g, 38 mmol) are added. The resulting suspension is stirred at 60° C. for 18 h, then water is added (100 mL) and the org. phase is collected. The aq. phase is extracted with EtOAc (100 mL) and the combined org. extracts are washed with water followed by brine, dried over MgSO4, filtered, evaporated and purified by CC (eluting with Heptane/EtOAc 9:1) to give 4-benzyloxy-3-ethyl-5-methyl-benzonitrile as a yellow oil (7.02 g); LC-MS: tR=1.11 min, [M+H]+=293.16.

Provenance & Evidence