Hydrochloric Acid → 2-(4-Methoxyphenyl)-2-methylpropanenitrile

Participants

Reaction Steps

To a suspension of sodium tert-butylate (21.54 g, 217.4 mmol) in dimethylformamide (37 mL) and tetrahydrofuran (37 mL) was added (4-methoxyphenyl)acetonitrile (8.00 g, 54.36 mmol) at 5° C. At the same temperature methyl iodide (13.54 mL) was added dropwise resulting in the formation of a light brown solid. The reaction mixture was diluted with dimethylformamide (15 mL) and tetrahydrofuran (15 mL). Stirring was continued at 10° C. for 1.5 h. The reaction mixture was cooled in a ice bath and 2N aqueous hydrochloric acid (100 mL) was added. The reaction mixture was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with aqueous saturated NaHCO3 solution (2×50 mL) and brine (50 mL). The extracts were dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (silica, n-heptane:dichloromethane=1:1). Yield: 7.6 g (43.4 mmol, 79.8%).

Provenance & Evidence