Methyl thiocyanate → 4-(4-n-Octylphenyl)-2-cyanophenol

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-(4-n-octylphenyl)phenol (2.82 g) in 1,2-dichloroethane (40 ml) is added a 2M borone trichloride - 1,2-dichloroethane solution (6 ml) under ice cooling, and thereto are further added methyl thiocyanate (0.82 ml) and aluminum chloride (1.33 g). The mixture is stirred at room temperature until aluminum chloride is dissolved, and is further stirred at 80° C. for 3 hours. After cooling, 4N aqueous sodium hydroxide solution (33 ml) is added to the reaction mixture, and the mixture is stirred at 75°-80° C. for 30 minutes. After cooling, the reaction mixture is washed with methylene chloride, and the aqueous layer is adjusted to pH 2 with 6N hydrochloric acid and then extracted with ether. The extract is dried and then ether is distilled off under reduced pressure. The crude crystal thus obtained is purified by silica gel column chromatography to give 4-(4-n-octylphenyl)-2-cyanophenol (2.03 g) of the following formula: ##STR32##

Provenance & Evidence