Ethyl phenylacetate → HCID 59627809, compound

Participants

Reaction Steps

To a mixture of [3-(methyloxy)phenyl]acetonitrile (2.0 g, 14 mmol) and ethyl phenylacetate (2.8 g, 17 mmol) in ethanol (4 mL) was added a sodium ethoxide solution (21%, 10.2 mL, 27 mmol), and the resulting mixture was heated at reflux for 18 hours. After cooling to room temperature, it was poured into a mixture of ice-water (50 mL). This aqueous mixture was washed with dichloromethane (3×20 mL) then acidified to pH 1. The acidified mixture was extracted with ethyl acetate (3×30 mL). The combined extract was washed with aqueous sodium bicarbonate solution, brine, dried over sodium sulfate, filtered and concentrated to give 2-[3-(methyloxy)phenyl]-3-oxo-4-phenylbutanenitrile as a brown oil (0.8 g, 3.4 mmol, 38% yield), MS (EI) for C17H15NO2: 266 (MH+).

Provenance & Evidence