Water → 4-Fluoro-2-nitrobenzoic acid

HRID 497984

Reaction equation

HRID 497984 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Mn]([O-])(=O)(=O)=[O:13].[K+].[OH2:18]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:13])=[O:18])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

4

Reactant 3

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

Product 1

HCID 27374164-Fluoro-2-nitrobenzoic acidYield 34%

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluoro-2-nitrotoluene (25.0 g, 161 mmol), potassium permanganate (102 g, 645 mmol) and water (500 mL) was heated and stirred at 100° C. for 3 hours. The solution was allowed to cool to room temperature, filtered through Celite to remove the insoluble derived from potassium permanganate. The filtrate was washed with diethylether and made acidic by the addition of conc. hydrochloric acid, and organic matter was extracted with diethylether. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (10.1 g, 34% yield).

Workup

  1. temperaturewas heated
  2. temperatureto cool to room temperature
  3. filtrationfiltered through Celite
  4. customto remove the
  5. washThe filtrate was washed with diethylether
  6. additionmade acidic by the addition of conc. hydrochloric acid, and organic matter
  7. extractionwas extracted with diethylether
  8. washThe extract was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-59c863e41f5d49709fe4035ed705cd81
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Linked notes

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