Water → 2-Fluoro-6-nitrobenzoic acid

HRID 1883033Notes

Reaction equation

HRID 1883033 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[C:9]=1[CH3:17].[OH2:18]>>[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[C:9]=1[C:17]([OH:2])=[O:18]

Participants

4

Reactant 3

HCID 962WaterHCID 698542-Fluoro-6-nitrotolueneHCID 516875Potassium Permanganate

Product 1

HCID 6037582-Fluoro-6-nitrobenzoic acid

Procedure

To a stirring suspension of potassium permanganate (102 g, 0.65 mol) in water (1.4 L) was added 2-fluoro-6-nitrotoluene. The reaction was heated at reflux for 4 h, cooled to room temperature, filtered, and washed with diethyl ether. The aqueous phase was acidified to pH 2 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to give 11.81 g (40%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 4 h
  3. filtrationfiltered
  4. washwashed with diethyl ether
  5. extractionextracted with ethyl acetate
  6. washThe organic phase was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give 11.81 g (40%)

Sources & evidence

ORD record
ord-e092ab4c831e4b4b8a089c0380588d21
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

Loading…