Water → 4-(3-Methyl-2-pyridinyl)benzoic acid

HRID 457914Notes

Reaction equation

HRID 457914 reaction equation
[CH3:1][C:2]1[C:3]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:17].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>CN(C=O)C>[CH3:1][C:2]1[C:3]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:17])=[O:15])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 21937278[4-(3-Methyl-2-pyridinyl)phenyl]methanol

Product 1

HCID 219373114-(3-Methyl-2-pyridinyl)benzoic acidYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [4-(3-methyl-2-pyridinyl)phenyl]methanol (12 g, 0.06 mol) in dry DMF (150 mL) was added pyridiniumdichromate (91 g, 0.24 mol) and stirred at RT for 3 days. The reaction mixture was poured into water and extracted with ethyl acetate (250 mL). The organic layer was washed with water, brine, dried and concentrated. The crude was purified by column chromatography over silica gel to give 4-(3-methyl-2-pyridinyl)benzoic acid (3 g, 25%) as white solid.

Workup

  1. extractionextracted with ethyl acetate (250 mL)
  2. washThe organic layer was washed with water, brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-24d2a296ddb94f28852bc0957d691470
Source dataset
uspto-grants-2007_03
Patent number
US07189754B2

Reaction notes

Loading…