Hydrochloric Acid → 3-chloro-5-(trifluoromethyl)benzoic Acid

HRID 1614419Notes

Reaction equation

HRID 1614419 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].C1C([N+]([O-])=O)=CC=C(O)C=1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 27737513-Chloro-2-fluoro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 38023623-chloro-5-(trifluoromethyl)benzoic Acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-Chloro-2-fluoro-5-(trifluoromethyl)benzoic acid and an equimolar amount of p-nitrophenol are stirred with an equimolar amount of anhydrous potassium carbonate in dimethylsulfoxide at 110° C. for 24 hours and then left overnight at room temperature. The mixture is then poured into dilute hydrochloric acid and the solid is recovered and purified by dissolving, washing and drying to give 4'-nitrophenoxy ether at the 2-position of 3-chloro-5-(trifluoromethyl)benzoic acid.

Workup

  1. customthe solid is recovered
  2. custompurified
  3. dissolutionby dissolving
  4. washwashing
  5. customdrying

Sources & evidence

ORD record
ord-3a70ecf1631345938d53cce05d7588da
Source dataset
uspto-grants-1993_03
Patent number
US05196593

Reaction notes

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