Water → 2-Nitro-4-(trifluoromethyl)phenol

HRID 1446881Notes

Reaction equation

HRID 1446881 reaction equation
[OH-:1].[Na+].Cl[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[N+:14]([O-:16])=[O:15].O>CS(C)=O>[N+:14]([C:5]1[CH:6]=[C:7]([C:10]([F:13])([F:12])[F:11])[CH:8]=[CH:9][C:4]=1[OH:1])([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 14798Sodium Hydroxide2×

Product 1

HCID 98162-Nitro-4-(trifluoromethyl)phenolYield 60.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Powdered sodium hydroxide (48 g) was added in portions over a period of 24 hours to a stirred solution of 4-chloro-3-nitrobenzotrifluoride (90 g) in dimethylsulfoxide (120 ml). After stirring the mixture vigorously for a further day another portion of powdered sodium hydroxide (4.8 g) was added and stirring was continued for a further 8 hours period. The mixture was poured into cold water (1 litre) and extracted with diethyl ether. The aqueous phase was acidified with concentrated hydrochloric acid, extracted with diethyl ether and the ethereal phase was washed with brine. The washed ethereal solution was dried over anhydrous magnesium sulfate and the solvent was evaporated to give the title compound as a brown oil (50 g).

Workup

  1. additionwas added
  2. extractionextracted with diethyl ether
  3. extractionextracted with diethyl ether
  4. washthe ethereal phase was washed with brine
  5. dry with materialThe washed ethereal solution was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5728d7ba39524137a3bf399000f9dadc
Source dataset
uspto-grants-1982_02
Patent number
US04314065

Reaction notes

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