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

HRID 1385335Notes

Reaction equation

HRID 1385335 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. Meter the addition was complete the reaction was quenched with saturated at sodium 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. additionMeter the addition
  3. customwas quenched with saturated at sodium 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-90c201239ed64b9d999c7de7a87112cf
Source dataset
uspto-grants-2001_07
Patent number
US06262113B1

Reaction notes

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