Ethanol → 2-(2-Methylnaphthalen-1-yl)acetonitrile

Participants

Reaction Conditions

Reaction Steps

1-Chloromethyl-2-methylnaphthalene (5.00 g, 26.3 mmol) and KCN (5.12 g, 78.8 mmol) were combined in H2O (20 mL) and EtOH (40 mL) in a round bottom flask fitted with a reflux condenser. The mix was stirred at 80° C. for 18 hours. TLC analysis (silica, 10% acetone-hexanes) indicated consumption of the starting chloromethylnaphthalene. The reaction was allowed to cool to room temperature and then was diluted with H2O. The dilution was extracted three times with EtOAc. The organic extracts were combined, washed with brine solution, dried over Na2SO4, decanted, and concentrated to give (2-methyl-naphthalen-1-yl)-acetonitrile in quantitative yield. MS (APCI) m/z 180.1 (M−H). 1H NMR (400 MHz) CDCl3 δ 7.96 (d, J=8.4 Hz, 1H), 7.85 (d, J=8.2 Hz, 1H), 7.77 (d, J=8.4 Hz, 1H), 7.61 (m ,1H), 7.50 (m, 1H), 7.34 (d, J=8.4, 1H), 4.07 (s, 2H), 2.58 (s, 3H).

Provenance & Evidence