Water → 4-Pyridin-3-yl-benzoic acid

HRID 1349009Notes

Reaction equation

HRID 1349009 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[CH:2]=1.[O-:14][Mn](=O)(=O)=O.[K+].[OH2:20]>N1C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[CH:9][C:10]([C:13]([OH:14])=[O:20])=[CH:11][CH:12]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 41331893-(4-methylphenyl)pyridine

Product 1

HCID 15152444-Pyridin-3-yl-benzoic acidYield 76%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 4-(3-pyridyl)toluene (35 g, 0.207 mol) in pyridine (400 ml) and water (400 ml) was added KMnO4 (163 g, 1.03 mol) in portions and refiuxed for 12 h. The reaction mixture was filtered through celite and acidified with cone. HCl. The product was washed with water and dried to give 4-(3pyridyl)benzoic acid (32 g, 76%) as a white solid. To a mixture of 4-(3-pyridyl)benzoic acid (22 g, 0.11 mol) in THF (2.51), mCPBA (152 g 0.44 mol, 50%) was added and stirred at RT for 12 h. The solid was filtered, and washed with TBF to give 4-(1-oxido-3-pyridinyl)benzoic acid (20 g, 86%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washThe product was washed with water
  3. customdried

Sources & evidence

ORD record
ord-8d1c68b93c9f402dbd9b5b606124444c
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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