2,6-Dimethyl-4-(hydroxymethyl)pyridine → 2,6-Dimethylpyridine-4-carbaldehyde

HRID 591802Notes

Reaction equation

HRID 591802 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([CH3:10])[CH:4]=1>C(O)C.O=[Mn]=O>[CH3:10][C:5]1[CH:4]=[C:3]([CH:2]=[O:1])[CH:8]=[C:7]([CH3:9])[N:6]=1

Participants

4

Reactant 1

HCID 38250772,6-Dimethyl-4-(hydroxymethyl)pyridine

Product 1

HCID 27630042,6-Dimethylpyridine-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 702EthanolSolvent

Procedure

4-Hydroxymethyl-2,6-dimethylpyridine (1.00 g, 7.28 mmol) was dissolved in ethanol (20 mL), and activated MnO2 (2.24 g, 21.8 mmol) was added; the reaction mixture was refluxed for 17 hours. The mixture was cooled and concentrated, purified by column chromatography (silica gel 230-400 mesh; 20% ethyl acetate in hexanes as eluent) to give 2,6-dimethyl-4-pyridinecarboxaldehyde as a yellow oil. Yield: 0.14 g (14%).

Workup

  1. temperaturethe reaction mixture was refluxed for 17 hours
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. custompurified by column chromatography (silica gel 230-400 mesh; 20% ethyl acetate in hexanes as eluent)

Sources & evidence

ORD record
ord-56d0f1afe30a44cdaee79ec598abc555
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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