Nitric Acid → 5-Chloro-4-methyl-2-nitrophenol

Participants

Reaction Conditions

Reaction Steps

247 g of 90% aqueous nitric acid was added drop-by-drop (over 2.5 hours) to a stirred mixture of 503.5 g of 4A and 2 liters of glacial acetic acid, at 5°-10° C. The resulting mixture was stirred at 10°-15° C. for 2 hours, and poured over 5 liters of ice water. The resulting mixture was stirred for 18 hours at room temperature, then extracted with a 2:3 v:v mixture of ether and hexane. The extract was washed with cold water, dried, and the solvents were evaporated. The residue was dissolved in 2 liters of ether, the solution was cooled to -60° C., held at that temperature for 30 minutes and filtered. The collected solid was washed with a cold (-60° C.) 1:1 v:v mixture of ether and hexane and air-dried to give 3-chloro-4-methyl-6-nitrophenol (4B), as a yellow solid, m.p.: 70°-71° C.

Provenance & Evidence