Water → 3-Fluoro-4-nitrobenzoic acid

HRID 1516748Notes

Reaction equation

HRID 1516748 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[Mn]([O-])(=O)(=O)=[O:13].[K+].[OH2:18]>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[C:11]([OH:13])=[O:18]

Participants

4

Reactant 3

HCID 962WaterHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 516875Potassium Permanganate

Product 1

HCID 2306533-Fluoro-4-nitrobenzoic acidYield 58%

Procedure

A mixture of 3-fluoro-4-nitrotoluene (10 g, 1 eq) and potassium permanganate (25.5 g, 2.5 eq) in water (1 l) is heated to reflux for 6 hours then cooled down to ambient temperature. The mixture is filtered on celite and the aqueous phase is washed twice with diethyl ether (2×300 ml). The aqueous phase is acidified with an aqueous solution of concentrated hydrochloric acid (12N) then concentrated under reduced pressure at 40° C. to a volume of approximately 300 ml. The precipitate formed is filtered then washed with petroleum ether and dried in order to produce the expected compound in the form of a white solid (6.9 g; 58% yield).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 6 hours
  3. filtrationThe mixture is filtered on celite
  4. washthe aqueous phase is washed twice with diethyl ether (2×300 ml)
  5. concentrationthen concentrated under reduced pressure at 40° C. to a volume of approximately 300 ml
  6. customThe precipitate formed
  7. filtrationis filtered
  8. washthen washed with petroleum ether
  9. customdried in order

Sources & evidence

ORD record
ord-4e33d19a7d8a44d3a21509d7595adad2
Source dataset
uspto-grants-2012_07
Patent number
US08227485B2

Reaction notes

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