Water → 4-Chloro-2-(4-trifluoromethylphenyl)benzoic acid

HRID 1267110Notes

Reaction equation

HRID 1267110 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:18])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH:7]=1.[O-:19][Mn](=O)(=O)=O.[K+].[OH2:25]>C(O)(C)(C)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:13]=2)[C:5]([C:18]([OH:19])=[O:25])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 185454465'-Chloro-2'-methyl4-trifluoromethyl-biphenyl

Product 1

HCID 185454704-Chloro-2-(4-trifluoromethylphenyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 5′-chloro-2′-methyl-4-trifluoromethyl-biphenyl (27 g) in a mixture of t-butanol (100 mL) and H2O (200 mL) was added portionwise KMnO4 (46.9 g). At the end of the addition, the mixture was heated under reflux for 16 hours, cooled to room temperature and filtered on celite. The filtrate was then acidified with concentrated HCl and the aqueous layer was extracted with AcOEt. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure to give the title compound (24 g) as white crystals.

Workup

  1. additionAt the end of the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 16 hours
  4. filtrationfiltered on celite
  5. extractionthe aqueous layer was extracted with AcOEt
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-440296c800904d35b2eb2e8a040b44d0
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

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