Water → 2-Nitro-4,6-bis(trifluoromethyl)phenol

HRID 267608Notes

Reaction equation

HRID 267608 reaction equation
[OH-:1].[Na+].[F:3][C:4]([F:20])([F:19])[C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([N+:15]([O-:17])=[O:16])[C:6]=1Cl.ClCl.O>CO>[F:3][C:4]([F:20])([F:19])[C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([N+:15]([O-:17])=[O:16])[C:6]=1[OH:1]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24526ChlorineHCID 108036882-Chloro-1-nitro-3,5-bis(trifluoromethyl)benzene

Product 1

HCID 213278352-Nitro-4,6-bis(trifluoromethyl)phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 168 g (4 moles +5% excess) of sodium hydroxide in 1000 ml methanol there were added portionwise, at 50°-65°C internal temperature, 586 g (2 moles) 2,4-bis-trifluoromethyl-6-nitrochlorobenzene; the reaction mixture, after completion of addition (about 1 hour) of the reactive chlorine compound, was boiled under reflux for one hour. After cooling, 700 ml of water were added to the mixture and unreacted starting materials were extracted once with 400 ml methylene chloride. The aquous phase was separated off, distinct acidification was effected with 20%-strength sulfuric acid; the 2,4-bis-trifluoromethyl-6-nitrophenol which separated was taken up in methylene chloride. The organic phase was dried over sodium sulfate. The 2,4-bis-trifluoromethyl-6-nitro-phenol remaining behind after methylene chloride had been distilled off was subjected to vacuum distillation. 480 g (87%) of the boiling pont 105°-106°C/20 mm Hg were obtained; refractive index nD20 : 1.4580.

Workup

  1. temperatureunder reflux for one hour
  2. temperatureAfter cooling
  3. extractionwere extracted once with 400 ml methylene chloride
  4. customThe aquous phase was separated off
  5. customthe 2,4-bis-trifluoromethyl-6-nitrophenol which separated
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. distillationThe 2,4-bis-trifluoromethyl-6-nitro-phenol remaining behind after methylene chloride had been distilled off
  8. distillationwas subjected to vacuum distillation
  9. custom480 g (87%) of the boiling pont 105°-106°C/20 mm Hg were obtained

Sources & evidence

ORD record
ord-12da0b8a1e364d69975e1ffee5c95704
Source dataset
uspto-grants-1976_03
Patent number
US03943180

Reaction notes

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