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

HRID 1419346Notes

Reaction equation

HRID 1419346 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-trifiuoromethylphenol 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-trifiuoromethylphenol was prepared
  2. additionAfter the addition
  3. customwas 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-8de14c4d6e5d4111a53f2a7bad1dd3b9
Source dataset
uspto-grants-1999_03
Patent number
US05886044

Reaction notes

Loading…