Water → 3-Chloro-4-nitrobenzoic acid

Temperature

90 °C

2-Chloro-4-methyl-1-nitro-benzene (1.2 g, 6.99 mmol) in a mixture of water and pyridine (2/1, 30 mL) was heated at 90° C. then potassium permanganate (5.2 g, 32.9 mmol) was added in 4 portions at intervals of 1.5 hours. The reaction mixture was heated at 90° C. for 8 hours and then more potassium permanganate (2 g) was added and the resulting mixture was stirred at 90° C. overnight. More potassium permanganate (2 g) was added and the resulting mixture was stirred at 90° C. for 1 hour, the solid was filtered off on a CELITE™ pad. Water (50 mL) was added to the filtrate; the resulting mixture was acidified until pH<2 and was extracted 3 times with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 1.19 g (84% yield) of 3-chloro-4-nitro-benzoic acid as a light yellow solid without further purifications

1. temperatureThe reaction mixture was heated at 90° C. for 8 hours
2. stirringthe resulting mixture was stirred at 90° C. for 1 hour
3. filtrationthe solid was filtered off on a CELITE™ pad
4. additionWater (50 mL) was added to the filtrate
5. extractionwas extracted 3 times with ethyl acetate
6. washThe combined organic extracts were washed with water and brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. customevaporated under reduced pressure

ORD record

ord-2cd34dfb78a7405ca5031de6dfd20d5d

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09255110B2