Hydrochloric Acid → 4-Chloro-2-methylbenzonitrile

Temperature

25 °C

Toluene (30 mL) and ice was added to the above copper cyanide solution and then the reaction mixture was stirred vigorously. The above diazonium salt solution was then slowly added to the reaction mixture. After the addition was complete, the reaction mixture was stirred at 0° C. for 30 minutes. The reaction mixture was then allowed to warm to room temperature (25° C.), and then stirred for another hour. The reaction mixture was then heated to 50° C. for 2 hours without stirring. The toluene phase and precipitate were then separated from the aqueous phase. To the toluene phase was added 10 mL concentrated HCl, 40 mL hot H2O, and FeCl3.6H2O (32 g, 0.118 mol) and this reaction mixture was then stirred overnight. The reaction mixture was then added to 200 mL H2O. The organic phase was then extracted with toluene, dried and evaporated under reduced pressure to produce 4-chloro-2-methylbenzonitrile as a dark brown oil.

1. additionAfter the addition
2. stirringthe reaction mixture was stirred at 0° C. for 30 minutes
3. stirringstirred for another hour
4. temperatureThe reaction mixture was then heated to 50° C. for 2 hours
5. stirringwithout stirring
6. customThe toluene phase and precipitate were then separated from the aqueous phase
7. stirringthis reaction mixture was then stirred overnight
8. extractionThe organic phase was then extracted with toluene
9. customdried
10. customevaporated under reduced pressure

ORD record

ord-a050c3ed24de4d4bae0c2d12fb26feb1

Source dataset

uspto-grants-1991_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05034410