Water → 3-Methoxy-5-(trifluoromethyl)phenol

HRID 1060474Notes

Reaction equation

HRID 1060474 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)N.N([O-])=[O:15].[Na+].O>Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:15])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6056715-(Trifluoromethyl)-m-anisidineHCID 23668193Sodium Nitrite

Product 1

HCID 225717083-Methoxy-5-(trifluoromethyl)phenolYield 71.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

3-Methoxy-5-(trifluoromethyl)aniline (5 g) was suspended in 20% HCl (200 mL), stirred for 30 min, cooled to 0-5° C. and diazotized with NaNO2 (2.17 g) added in small portions. The mixture was stirred for 30 min at that temperature and added dropwise to boiling water (200 mL). The mixture was refluxed for 15 min, allowed to cool to room temperature and extracted with AcOEt, dried (MgSO4), filtered and evaporated. The residue was then purified by column chromatography (silica gel; eluent: hexane and AcOEt) to give 3-methoxy-5-(trifluoromethyl)phenol (3.6 g)

Workup

  1. additionadded in small portions
  2. stirringThe mixture was stirred for 30 min at that temperature
  3. additionadded dropwise
  4. temperatureThe mixture was refluxed for 15 min
  5. temperatureto cool to room temperature
  6. extractionextracted with AcOEt
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was then purified by column chromatography (silica gel; eluent: hexane and AcOEt)

Sources & evidence

ORD record
ord-87ccdd6664a24e4ebfd374cfc4ca8c13
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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