Methyl thiocyanate → HCID 20077557, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-ethylphenol (2.44 g) in dichloromethane (10 ml), was added to a stirred, ice-cooled, solution of 1M boron trichloride in dichloromethane (24 ml) under argon, followed by methylthiocyanate (1.64 ml), and then anhydrous aluminium chloride (2.66 g). The mixture was stirred for 1 hour at 4° C., then heated at reflux (bath temperature 60° C.) for 4 hours and finally stirred for 16 hours at ambient temperature. The mixture was added cautiously to a stirred, ice-cooled, 4M sodium hydroxide solution and the resultant mixture heated at 70° C. for 30 minutes then cooled. The aqueous phase was separated, washed with dichloromethane (2×25 ml), then acidified to pH 2 with 6M hydrochloric acid and extracted with ethyl acetate (3×75 ml). The combined organic extracts were washed with saturated brine (3×50 ml), dried (MgSO4) and the solvent removed in vacuo to give a brown solid. Purification by flash chromatography, eluting with 20% v/v ethyl acetate in hexane, followed by recrystallisation from hexane gave 2-cyano-4-ethylphenol (A) (2.56 g), m.p. 95°-98° C.; NMR: 1.21 (3H, t, J=7 Hz), 2.59 (2H, q, J=7 Hz), 5.70 (1H, b), 6.90 (1H, m), 7.29 (2H, m).

Provenance & Evidence