Water → 4-(2-Pyridyl)Benzoic Acid

HRID 459480Notes

Reaction equation

HRID 459480 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:3][CH:2]=1.[Mn]([O-])(=O)(=O)=[O:15].[K+].[OH2:20]>>[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:4]1[CH:5]=[CH:6][C:1]([C:13]([OH:15])=[O:20])=[CH:2][CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 782192-(p-Tolyl)pyridineHCID 516875Potassium Permanganate

Product 1

HCID 8216924-(2-Pyridyl)Benzoic Acid

Procedure

2-(p-Toluyl)pyridine (17.2 g) was suspended in water (200 ml), and to the suspension potassium permanganate (21.0 g) was added. The mixture was heated under reflux for 18 hours. After the reaction mixture was allowed to cool, and insoluble matter was removed by filtration, dichloromethane was added to the filtrate, and the resultant water layer was separated and acidified with 2N hydrochloric acid. The solution was concentrated, and precipitate was collected by filtration to obtain the title compound (7.07 g) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. temperatureto cool
  4. custominsoluble matter was removed by filtration, dichloromethane
  5. additionwas added to the filtrate
  6. customthe resultant water layer was separated
  7. concentrationThe solution was concentrated
  8. filtrationprecipitate was collected by filtration

Sources & evidence

ORD record
ord-e0acf542ff2d4cf9a0cad3ffa19bad8b
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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