Nitric Acid → 4-Fluoro-2-methyl-5-nitrobenzoic acid

HRID 1942543Notes

Reaction equation

HRID 1942543 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[F:1][C:2]1[C:10]([N+:12]([O-:14])=[O:13])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 38606394-Fluoro-2-methylbenzoic acid

Product 1

HCID 223131014-Fluoro-2-methyl-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a suspension of 4-fluoro-2-methylbenzoic acid (32.5 g) in conc. sulfuric acid (50 ml) was added dropwise conc. nitric acid (8.4 ml) at 0° C., and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into ice-water (500 ml), and the mixture was extracted with diisopropyl ether (300 ml), and the organic layer was washed with water, and a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, concentrated under reduced pressure to give the title compound (40.0 g).

Workup

  1. extractionthe mixture was extracted with diisopropyl ether (300 ml)
  2. washthe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-74c25b69eee74789b39fa7d8667c3e25
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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