(4,6-Dimethylpyridin-2-yl)methanol → 4,6-Dimethylpyridine-2-carbaldehyde

HRID 1910754Notes

Reaction equation

HRID 1910754 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH2:9][OH:10])[CH:3]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH:9]=[O:10])[CH:3]=1

Participants

4

Reactant 1

HCID 4296719(4,6-Dimethylpyridin-2-yl)methanol

Product 1

HCID 2255194,6-Dimethylpyridine-2-carbaldehydeYield 51%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Manganese dioxide (3.17 g, 36.5 mmol) was added to a solution of (4,6-dimethyl-pyridin-2-yl)-methanol (1.0 g, 7.30 mmol) in chloroform (30 mL) and heated at reflux overnight. The reaction mixture was cooled to 0° C. and filtered over celite, washing with further chloroform. The filtrate was evaporated to give a residue which was purified by column chromatography over silica gel (60-120 mesh) using 10% ethyl acetate in hexane as eluent to afford 4,6-dimethyl-pyridine-2-carbaldehyde (0.5 g, 51%) as a light brown liquid.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. filtrationfiltered over celite
  4. washwashing with further chloroform
  5. customThe filtrate was evaporated
  6. customto give a residue which
  7. customwas purified by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-46863e50c02f4a3ea8d58186ffd3ebd2
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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