Acetonitrile → 4-(Cyanoacetyl)benzonitrile

Participants

Reaction Steps

A solution of acetonitrile (9.22 mL, 176 mmol) in tetrahydrofuran (320 mL) was added to sodium hydride (60% dispersion in mineral oil) (11.80 g, 294 mmol). This mixture was stirred at room temperature for 15 minutes, and then 4-Cyano-benzoic acid methyl ester (23.70 g, 147 mmol) was added. The reaction mixture was stirred at 60° C. for 2 hours, And then quenched onto an aqueous solution of hydrochloric acid (2M, 500 mL), and extracted with ethyl acetate (3×500 mL). The combined organic extracts were washed with brine (500 mL), dried over magnesium sulphate, filtered and evaporated under reduced pressure. This residue was triturated with 20% ethyl acetate in heptane to give the title compound as a solid (23.17 g, 93%). ESCI MS m/z 169 [M−H]−

Provenance & Evidence