3-Methoxy-5-nitrobenzotrifluoride → 3-Hydroxy-5-nitrobenzotrifluoride

HRID 1786314Notes

Reaction equation

HRID 1786314 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1.Cl.N1C=CC=CC=1>>[N+:13]([C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=1)([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 5205973-Methoxy-5-nitrobenzotrifluorideHCID 10176127Pyridinium chloride

Product 1

HCID 27562513-Hydroxy-5-nitrobenzotrifluoride

Conditions

Temperature
210 °C

Procedure

1-Methoxy-3-nitro-5-trifluoromethyl-benzene (10 g, Aldrich) and pyridine-HCl (41.8 g, Aldrich) were mixed together and heated neat at 210° C. in an open flask. After 2.5 h the mixture was cooled to RT and partitioned between 1N HCl and EtOAc. The EtOAc fraction was washed with 1N HCl (4×), brine (1×), dried with Na2SO4, filtered and concentrated in vacuo to form 3-nitro-5-trifluoromethyl-phenol as an off-white solid.

Workup

  1. temperatureAfter 2.5 h the mixture was cooled to RT
  2. custompartitioned between 1N HCl and EtOAc
  3. washThe EtOAc fraction was washed with 1N HCl (4×), brine (1×)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4f37722ccab48ea9c643fffa08d8fae
Source dataset
uspto-grants-2009_03
Patent number
US07507748B2

Reaction notes

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