Potassium Permanganate → 5-(Trifluoromethoxy)pyridine-2-carboxylic acid

HRID 622602Notes

Reaction equation

HRID 622602 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][OH:11])=[N:8][CH:9]=1.[Mn]([O-])(=O)(=O)=[O:15].[K+]>O>[F:13][C:2]([F:1])([F:12])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([OH:15])=[O:11])=[N:8][CH:9]=1

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 19860740[5-(Trifluoromethoxy)-2-pyridyl]methanol

Product 1

HCID 198607385-(Trifluoromethoxy)pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3 g 5-trifluoromethoxy-2-pyridinemethanol is vigorously stirred in 120 mL water at 5° C. To this mixture is added in several portions 3.0 g potassium permanganate during which time the temperature rises to 25° C. After a further 30 minutes at 25° C., the mixture is filtered, the solid washed several times with water, the filtrate and washings combined and the pH adjusted to 5. The solution is concentrated to a small volume and extracted with ethyl acetate several times. The extract is washed, dried and concentrated to give 5-trifluoromethoxy-2-pyridinecarboxylic acid.

Workup

  1. customrises to 25° C
  2. filtrationthe mixture is filtered
  3. washthe solid washed several times with water
  4. concentrationThe solution is concentrated to a small volume
  5. extractionextracted with ethyl acetate several times
  6. washThe extract is washed
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3e4806fb0a284fa18add36b8f0349e50
Source dataset
uspto-grants-1988_09
Patent number
US04772311

Reaction notes

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