Dichloromethane → (3-Hydroxy-6-methyl-pyridin-2-yl)-phenyl-methanone

HRID 228755Notes

Reaction equation

HRID 228755 reaction equation
[OH:1][CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[C:5]([CH3:10])[N:4]=1.ClCCl>CO.[O-2].[O-2].[Mn+4]>[OH:9][C:8]1[C:3]([C:2]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:1])=[N:4][C:5]([CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 230783712-(Hydroxyphenyl-methyl)-6-methyl-pyridin-3-ol

Product 1

HCID 23078462(3-Hydroxy-6-methyl-pyridin-2-yl)-phenyl-methanoneYield 80.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolvent

Procedure

2-(Hydroxy-phenyl-methyl)-6-methyl-pyridin-3-ol (553 mg) was dissolved in methanol (3 ml) and dichloromethane (9 ml) to prepare a solution. Manganese dioxide (2.05 g) was added to the solution, and the mixture was stirred at room temperature overnight. The reaction solution was filtered through Celite and was then washed with chloroform and methanol. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-acetone to give (3-hydroxy-6-methyl-pyridin-2-yl)-phenyl-methanone (439 mg, yield 80%).

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. washwas then washed with chloroform and methanol
  3. customThe solvent was removed by distillation under the reduced pressure
  4. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-c31a661dcc4d452bbf7cdfb82b918008
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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