3,4-Dimethoxybenzeneacetonitrile → 2-[3,4-Bis(methyloxy)phenyl]-4-(methyloxy)-3-oxobutanenitrile

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Reaction Steps

To a mixture of [3,4-bis(methyloxy)phenyl]acetonitrile (2.0 g, 11 mmol) and ethyl (methyloxy)acetate (1.65 g, 14 mmol) in ethanol (4 mL) was added a sodium ethoxide solution (21%, 8.4 mL, 23 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) to remove all non-basic organic impurities, and then it was acidified to pH of 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-[3,4-bis(methyloxy)phenyl]-4-(methyloxy)-3-oxobutanenitrile as a brown oil (1.8 g, 7.2 mmol, 66% yield), MS (EI) for C13H15NO4: 250 (MH+).

Provenance & Evidence