Acetone Cyanohydrin → Methyl 3-(cyanomethyl)benzoate

Participants

Reaction Steps

1,1,3,3-Tetramethylguanidine (3.21 ml, 25.6 mmol) was added dropwise to a solution of methyl 3-bromomethylbenzoate (2.80 g, 12.2 mmol) and acetone cyanohydrin (1.59 ml, 18.3 mmol) in acetonitrile (40 ml) at room temperature. The reaction was stirred for 3 days and the solvent then removed under reduced pressure. The resulting brown oil was purified by column chromatography on silica gel using ethyl acetate:pentane (50:50) as eluant to afford the title compound as a clear oil, 1.80 g.

Provenance & Evidence