Water → HCID 53956374, compound

2-Nitro-4-pentafluoroethyltoluene (56.6 g) and pyridine (170 ml) were added to a stirred solution of sodium hydroxide (10.0 g) in water (500 ml). The mixture was stirred and heated at reflux and potassium permanganate (174 g) was added portionwise. The mixture was stirred and heated at reflux for 1 hour until the purple colouration had disappeared. After cooling, the mixture was filtered and the solid was washed with water (3×100 ml) and ether (300 ml). The layers were separated and the aqueous layer was washed with ether and acidified to pH 1. It was extracted with ether (3×300 ml) and the combined extracts were washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give 2-nitro-4-pentafluoroethylbenzoic acid (51.6 g) as a white solid mp 124°-135° C.

1. temperatureheated
2. temperatureat reflux
3. stirringThe mixture was stirred
4. temperatureheated
5. temperatureat reflux for 1 hour until the purple colouration
6. temperatureAfter cooling
7. filtrationthe mixture was filtered
8. washthe solid was washed with water (3×100 ml) and ether (300 ml)
9. customThe layers were separated
10. washthe aqueous layer was washed with ether
11. extractionIt was extracted with ether (3×300 ml)
12. washthe combined extracts were washed with water
13. dry with materialdried (anhydrous magnesium sulphate)
14. filtrationfiltered
15. customThe filtrate was evaporated to dryness

ORD record

ord-d655045780b641e8965d4b5be9d9456c

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05747424