Benzyl Alcohol → 3,5-Dimethylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

An oven dried screw cap test tube was charged with NaCN (140 mg, 2.857 mmol) dried KI (79 mg, 0.476 mmol, 20 mol %) and CuI (45 mg, 0.236 mmol, 10 mol %), evacuated and backfilled with argon three times. Anhydrous toluene (1550 μl), N,N′-dimethylethylenediamine (255 μl, 2.395 mmol), 1-Bromo-3,5-dimethyl-benzene (255 μl, 1.877 mmol), and benzyl alcohol (155 μl, 1.498 mmol) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 12 h. The resulting yellow color suspension was cooled to room temperature, 2 mL of ethyl acetate, 250 μl of n-dodecane as internal standard, 1 mL of ammonium hydroxide 30% and 1 mL of water were added. The mixture was stirred at 25° C. for 10 min then the organic layer was washed with 1 mL of water and dried over MgSO4. The GC analysis showed a conversion of 91% with a yield of the title product, calculated vs internal standard, of 88%.

Provenance & Evidence