Water → 3-Fluoro-4-nitrobenzoic acid

HRID 1784286Notes

Reaction equation

HRID 1784286 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 under 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, at 0° C., with a solution of concentrated hydrochloric acid 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. temperatureunder 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. customis acidified, at 0° C., with a solution of concentrated hydrochloric acid
  6. concentrationthen concentrated under reduced pressure at 40° C. to a volume of approximately 300 ml
  7. customThe precipitate formed
  8. filtrationis filtered
  9. washthen washed with petroleum ether
  10. customdried in order

Sources & evidence

ORD record
ord-2a548b80b3df4b579cdecb96da60aa24
Source dataset
uspto-grants-2009_03
Patent number
US07501525B2

Reaction notes

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