Hydrochloric Acid → 2-Nitro-4-(trifluoromethyl)phenol
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].O.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
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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 200 ml of dimethyl sulfoxide at room temperature. The mixture was allowed to stand overnight, then poured into 1.5 liters of cold water. The resulting 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 and the mixture was extracted with petroleum ether. The water layer was acidified with concentrated hydrochloric acid and the resulting oil was separated and dissolved in ether. The solution was dried (MgSO4) and stripped of solvent to give 2-nitro-4-(trifluoromethyl)phenol (7A).
Workup
- customAn oil formed
- customit was separated
- dissolutiondissolved in ether
- dry with materialThe solution was dried (MgSO4)
- additionThe residue was mixed with cold sodium hydroxide solution
- extractionthe mixture was extracted with petroleum ether
- customthe resulting oil was separated
- dissolutiondissolved in ether
- dry with materialThe solution was dried (MgSO4)
Sources & evidence
- ORD record
- ord-0dfc529088bb47c995e8a5bd9d279065
- Source dataset
- uspto-grants-1979_12
- Patent number
- US04180572
Reaction notes
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