Chloroform → 2,6-Dimethylphenyl isocyanide

Participants

Reaction Steps

A reaction flask was charged with 48.4 g (0.4 mole) of 2,6-dimethylaniline, 50 ml of chloroform, 50 ml of methylene chloride, and 1.0 g of methyl tricaprylylammonium chloride (designated by the trade name "Aliquat 336®" and obtained from General Mills Co., Chemical Division, Kankakee, Ill.). The flask was placed in a water bath at room temperature. As the flask contents were vigorously stirred, 150 ml of 50% aqueous sodium hydroxide was added. Stirring was continued overnight. The reaction mixture was then poured into 400 ml of ice water and extracted with 200 ml of diethyl ether. The ether phase was separated and washed with water, dried, and stripped. The residue was then extracted with 200 ml of hot hexane which was subsequently stirred with 20 g of Florisil® silica absorbent material and filtered. The filtrate was chilled in a dry ice/acetone bath and filtered to yield 35.2 g of a tan-colored solid. The structure indicated by the above title was confirmed by infrared spectra, nuclear magnetic resonance, and mass spectroscopy.

Provenance & Evidence