Hydrochloric Acid → 2-Nitro-4-(trifluoromethyl)phenol

HRID 1660492Notes

Reaction equation

HRID 1660492 reaction equation
[OH-:1].[Na+].[N+:3]([C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:7]=1Cl)([O-:5])=[O:4].Cl>CS(C)=O>[N+:3]([C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:7]=1[OH:1])([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 14798Sodium Hydroxide

Product 1

HCID 98162-Nitro-4-(trifluoromethyl)phenol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

87.6 g of finely powdered sodium hydroxide was added in portions over an 8-hour period to a stirred solution of 164.0 g of 2-nitro-4-(trifluoromethyl)chlorobenzene in 220 ml of dimethyl sulfoxide at room temperature. The mixture was acidified to pH 1 with concentrated hydrochloric acid. An oil formed; it was separated and dissolved in ether. The solution was dried (MgSO4) and stripped of solvent under reduced pressure. The residue was mixed with cold sodium hydroxide solution. The mixture was extracted with petroleum ether. The water layer was acidified with concentrated hydrochloric acid. An oil that formed was separated and dissolved in ether. The solution was dried (MgSO4) and stripped of solvent to give 2-nitro-4-(trifluoromethyl)phenol (A).

Workup

  1. customAn oil formed
  2. customit was separated
  3. dissolutiondissolved in ether
  4. dry with materialThe solution was dried (MgSO4)
  5. additionThe residue was mixed with cold sodium hydroxide solution
  6. extractionThe mixture was extracted with petroleum ether
  7. customAn oil that formed
  8. customwas separated
  9. dissolutiondissolved in ether
  10. dry with materialThe solution was dried (MgSO4)

Sources & evidence

ORD record
ord-753ade7078f14dbf877c866ef7d36ea5
Source dataset
uspto-grants-1981_12
Patent number
US04308276

Reaction notes

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