Water → 4-Fluoro-2-nitrobenzoic acid

HRID 988607Notes

Reaction equation

HRID 988607 reaction equation
[O-:1][Mn](=O)(=O)=O.[K+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1.[OH2:18]>>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:1])=[O:18])=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1

Participants

4

Reactant 3

HCID 962WaterHCID 679654-Fluoro-2-nitrotolueneHCID 516875Potassium Permanganate

Product 1

HCID 27374164-Fluoro-2-nitrobenzoic acidYield 34%

Procedure

To a stirring solution of KMnO4 (76 g, 483 mmol) in water (1 L) was added 4-fluoro-2-nitrotoluene and the solution was heated to reflux. After 4 h, the hot mixture was filtered and the filtrate was cooled with ice, washed with diethyl ether, acidified with conc HCl, and then extracted twice with diethyl ether. The combined ether extracts were washed with brine, dried with MgSO4, filtered and concentrated in vacuo to give 12.07 g (34%) of a white solid.

Workup

  1. temperaturethe solution was heated to reflux
  2. filtrationthe hot mixture was filtered
  3. temperaturethe filtrate was cooled with ice
  4. washwashed with diethyl ether
  5. extractionextracted twice with diethyl ether
  6. washThe combined ether extracts were washed with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12fdaf381e594034950a9526df649d2b
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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