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

HRID 1956619Notes

Reaction equation

HRID 1956619 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:6]=1>>[N+:1]([C:10]1[CH:5]=[CH:6][C:7]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:9]=1[OH:11])([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 a,a,a-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. 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-e8563d57feac44d18f07a2f737bddbae
Source dataset
uspto-grants-1998_07
Patent number
US05780483

Reaction notes

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