Iodocyclohexane → 2-hydroxy-5-(trifluoromethyl)benzoic Acid

HRID 1623735Notes

Reaction equation

HRID 1623735 reaction equation
IC1CCCCC1.C[O:9][C:10]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]>CN(C)C=O>[OH:9][C:10]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 12289IodocyclohexaneHCID 135859092-Methoxy-5-(trifluoromethyl)benzoic acid

Product 1

HCID 111172032-hydroxy-5-(trifluoromethyl)benzoic Acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodocyclohexane (29.4 ml, 227 mmol) was added to a solution of 2-(methyloxy)-5-(trifluoromethyl)benzoic acid (5 g, 22.71 mmol) in N,N-dimethylformamide (25 ml), and the mixture was heated under reflux for 4 hours. After cooling, the reaction was evaporated under reduced pressure on a buchi. The residue was triturated with cyclohexane, and the solid obtained was filtered, washed with cyclohexane and dried in air under vacuum. 4.2 g

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling
  4. customthe reaction was evaporated under reduced pressure on a buchi
  5. customThe residue was triturated with cyclohexane
  6. customthe solid obtained
  7. filtrationwas filtered
  8. washwashed with cyclohexane
  9. customdried in air under vacuum

Sources & evidence

ORD record
ord-f8886c56aeba4aa59310375888276a3c
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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