Selenium Dioxide → 6-(O-Tolyl)picolinaldehyde

HRID 2309733Notes

Reaction equation

HRID 2309733 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[CH:10][CH:9]=1.[Se](=O)=[O:16]>O1CCOCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([CH:14]=[O:16])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 212757512-Methyl-6-(2-methylphenyl)pyridine

Product 1

HCID 201846846-(O-Tolyl)picolinaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.8 g of 6-(2-methylphenyl)-2-methylpyridine was dissolved in 180 ml 1,4-dioxane, 1.4 g of selenium dioxide (Aldrich Gold Label) was added and the mixture refluxed for 36 hours. The solids were removed by filtration. Ether was added and the organic extracts washed five times with 100 ml water. After drying over magnesium sulfate and evaporation, 6-(2-methylphenyl)-2-pyridinecarboxaldehyde was afforded as a pale yellow oil (1.4 g).

Workup

  1. temperaturethe mixture refluxed for 36 hours
  2. customThe solids were removed by filtration
  3. additionEther was added
  4. washthe organic extracts washed five times with 100 ml water
  5. dry with materialAfter drying over magnesium sulfate and evaporation

Sources & evidence

ORD record
ord-7fa715b0cfaf443d98c23c0dfcb730c6
Source dataset
uspto-grants-1987_09
Patent number
US04696938

Reaction notes

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