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

HRID 491583Notes

Reaction equation

HRID 491583 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:12]([F:15])([F:14])[F:13])=[C:8]([O:10]C)[CH:9]=1)([O-:3])=[O:2].Cl.N1C=CC=CC=1.Cl>CCOC(C)=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:12]([F:13])([F:14])[F:15])=[C:8]([OH:10])[CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 177559612-Methoxy-4-nitro-1-(trifluoromethyl)benzene

Product 1

HCID 219595865-Nitro-2-(trifluoromethyl)phenol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
210 °C

Procedure

5-Nitro-2-trifluoromethylanisole (10.7 g, 48.5 mmol) and pyridine hydrochloride (44.9 g, 388 mmol) were combined in a round-bottom flask and heated at 210° C. for 2 h. The reaction was cooled to RT and dissolved into 6 N HCl and EtOAc. The layers were separated, and the organic layer was washed 4× with 2 N HCl and once with brine, dried over Na2SO4, filtered, and concentrated in vacuo, to yield the title compound as a dark red solid.

Workup

  1. temperatureThe reaction was cooled to RT
  2. customThe layers were separated
  3. washthe organic layer was washed 4× with 2 N HCl
  4. dry with materialonce with brine, dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b8c2f6b0594644188f670488e5f133e0
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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