Methyl iodide → 4-(Methoxymethyl)benzonitrile

Participants

Reaction Steps

To a solution of 4-(hydroxymethyl)benzonitrile (5 g, 37.6 mmol) in DMF (100 mL) was added iodomethane (7.03 mL, 113 mmol) and NaH (1.502 g, 37.6 mmol). The reaction aged at rt for 2 h and was then partitioned between EtOAc and H2O. The organic layer was separated and washed with H2O (2×), brine, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography on silica gel gradient eluted with 0-20% EtOAc/hexane to afford the title compound. HPLC/MS: 148.1 (M+1); Rt=2.28 min.

Provenance & Evidence