Nitric Acid → 2-Nitro-5-(trifluoromethyl)phenol

HRID 567962Notes

Reaction equation

HRID 567962 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]=[C:9]([OH:13])[CH:8]=1>>[N+:1]([C:10]1[CH:11]=[CH:12][C:7]([C:6]([F:15])([F:14])[F:5])=[CH:8][C:9]=1[OH:13])([O-:4])=[O:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 73763-(Trifluoromethyl)phenol

Product 1

HCID 140916902-Nitro-5-(trifluoromethyl)phenolYield 27%

Procedure

2-Nitro-5-trifluoromethylphenol was prepared by adding concentrated HNO3 (6 mL) drop-wise to α,α,α-trifluoro-m-cresol (5 g, 30.8 mmol) at room temperature. After the addition was complete. the reaction was quenched with saturated ammonium acetate and extracted with EtOAc. The organic was separated, dried over sodium sulfate and filtered. Concentration of the solution in vacuo afforded an oil which was purified by column chromatography (gradient 100% hexane to 50% EtOAc/hexanes) to afford the titled compound as an oil(1.7 g, 27%). 1H NMR (CDCl3): 10.6 (s, 1H, OH), 8.26(d, 1H, J=7.8 Hz), 7.45(s, 1H, arom), 7.26(d, 1H, J=7.8 Hz).

Workup

  1. custom2-Nitro-5-trifluoromethylphenol was prepared
  2. additionAfter the addition
  3. customthe reaction was quenched with saturated ammonium acetate
  4. extractionextracted with EtOAc
  5. customThe organic was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customConcentration of the solution in vacuo afforded an oil which
  9. customwas purified by column chromatography (gradient 100% hexane to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9ad5b50795ba4db78e01af14024e0f20
Source dataset
uspto-grants-2001_01
Patent number
US06180675B2

Reaction notes

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