Hydrochloric Acid → 2-Chloro-6-methylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

Sodium cyanide (65 g, 1.33 mol) in 100 ml of water is added to cuprous chloride (49.5 g, 0.5 mol) in 200 ml of water while stirring mechanically in a 5 l. 3-necked flask. Evolution of heat resulted and the cuprous chloride dissolves. This is then cooled in an ice bath to 0° C. A milky suspension of cuprous cyanide results. To this is added 100 ml of toluene. 6 N Hydrochloric acid (140 ml) is added slowly to 6-chloro-2-methylbenzenamine (56 g, 0.4 mol) while swirling in a 2 l. erlenmeyer flask and keeping the temperature at 0° C. A solution of sodium nitrite (28 g, 0.4 mol) in 80 ml of water is added dropwise to the hydrochloride suspension. Ice is added, when required, keeping the temperature at 0° C. Anhydrous sodium carbonate is added until the diazonium hydrochloride solution is neutral to pH paper. This is then added slowly to the cold stirring cuprous cyanide suspension, the temperature not being allowed to rise above 5° C. The reaction is then stirred at 0°-5° C. for 0.75 hr, allowed to reach room temperature over a 3 hr period and then heated on the steam bath at 50° C. After remaining at room temperature overnight, the product is steam distilled off. The distillate (3.5 l.) is extracted with benzene, dried and evaporated to give 2.8 g of the title compound, nmr (CDCl3) δ 2.55 (s, 3H) and 7.3 (m, 3H).

Provenance & Evidence