Nitric Acid → 2-Nitro-6-(trifluoromethyl)phenol

HRID 1064821Notes

Reaction equation

HRID 1064821 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]([F:15])([F:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13]>C(#N)C.O>[N+:1]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:6]([F:15])([F:14])[F:5])[C:8]=1[OH:13])([O-:4])=[O:2]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 679582-Trifluoromethylphenol

Product 1

HCID 9018342-Nitro-6-(trifluoromethyl)phenolYield 33.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Acetyl nitrate obtained mixing acetyl anhydride (3.30 g, 33 mmol) with fuming nitric acid (2.05 g, 33 mmol) at 0° C. was dropped into a solution of 2-trifluoromethylphenol (4.86 mg, 30 mmol) in acetonitrile (60 ml) at 0° C. followed by stirring for 10 minutes. The reaction solution was diluted with water and extracted with ether. The organic layer was washed with water and a saturated sodium chloride solution successively and dried and the solvent was evaporated therefrom. The residue was purified by a silica gel column chromatography (60 g of silica gel; developing solvent, hexane:methylene chloride=5:1) to provide 2.1 g (yield 33%) of 2-nitro-6-trifluoromethylphenol as pale yellow crystals.

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride solution successively and dried
  4. customthe solvent was evaporated
  5. customThe residue was purified by a silica gel column chromatography (60 g of silica gel; developing solvent, hexane:methylene chloride=5:1)

Sources & evidence

ORD record
ord-4b5fbafb0f2843658450a95026941711
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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