O-Cresol → HCID 4739205, compound

Participants

Reaction Steps

A solution of o-cresol (5.4 g, 50.7 mmol) in DMSO (10 mL) was added dropwise to a stirred mixture of 60% oil dispersion sodium hydride (2.02 g, 50.5 mmol) in DMSO (20 mL). After stirring for 1 hour at ambient temperature, a solution of p-fluorobenzaldehyde (5.36 mL, 50 mmol) in DMSO (10 mL) was added dropwise. After the addition was complete, the reaction mixture was gradually heated to 140-160° C. and maintained at that temperature for 1 hour. The reaction mixture was poured into ice-water and extracted with ether. The combined organic extracts were washed successively with ice-cold dilute aqueous sodium hydroxide solution, dilute aqueous hydrochloric acid solution, water and saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated to give a brown liquid. Chromatography on silica gel eluting with 95:5 hexane-ethyl acetate afforded 6.1 g (51%).of the title compound. 1H NMR (CDCl3, 300MHz) δ 2.19 (s, 3H), 6.98 (m, 3H), 7.2 (m, 3H), 7.82 (m, 2H), 9.9 (s, 1H). MS (DCl/NH3) m/e 213 (M+H)+.

Provenance & Evidence