m-Chloroperbenzoic acid → HCID 21937224, compound

HRID 1349010Notes

Reaction equation

HRID 1349010 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)[CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:24])C=1>C1COCC1>[O-:24][N+:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15152444-Pyridin-3-yl-benzoic acid

Product 1

HCID 21937224HCID 21937224, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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. additionwas added
  2. filtrationThe solid was filtered
  3. washwashed with TBF

Sources & evidence

ORD record
ord-98b0ceb9c5014a9ebd7b5bff20794287
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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