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

Temperature

-60 °C

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.

1. stirringThe resulting mixture was stirred for 18 hours at room temperature
2. extractionextracted with a 2:3 v
3. additionv mixture of ether and hexane
4. washThe extract was washed with cold water
5. customdried
6. customthe solvents were evaporated
7. dissolutionThe residue was dissolved in 2 liters of ether
8. waitheld at that temperature for 30 minutes
9. filtrationfiltered
10. washThe collected solid was washed with a cold (-60° C.) 1:1 v
11. additionv mixture of ether and hexane
12. customair-dried

ORD record

ord-b3b3a2bee2984b84b9a6dce314fb83f1

Source dataset

uspto-grants-1985_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04558040