Hydrogen Peroxide → 2,5-Dimethylpyridin-1-ium-1-olate

HRID 703174Notes

Reaction equation

HRID 703174 reaction equation
[OH:1]O.[N:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[CH3:10]>C(O)(=O)C>[CH3:10][C:4]1[CH:5]=[CH:6][C:7]([CH3:9])=[CH:8][N+:3]=1[O-:1]

Participants

4

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 115262,5-Dimethylpyridine

Product 1

HCID 5717732,5-Dimethylpyridin-1-ium-1-olate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

400 ml of 30% hydrogen peroxide were added dropwise at room temperature to 321.5 g of 2,5-lutidine (2,5-dimethylpyridine) in 1800 ml of glacial acetic acid. The solution was stirred at 80° overnight, then cooled to 40° , treated once more with 400 ml of 30% hydrogen peroxide and heated to 80° for a further 24 hours. After evaporation in vacuo the residue was dissolved in 300 ml of water. The solution was made basic with concentrated sodium hydroxide solution while cooling, saturated with sodium chloride and extracted three times with 1 1 of methylene chloride. The organic extracts were dried over sodium sulfate and evaporated in vacuo. There was obtained 2,5-dimethylpyridine 1-oxide in the form of an oil.

Workup

  1. temperaturecooled to 40°
  2. temperatureheated to 80° for a further 24 hours
  3. customAfter evaporation in vacuo the residue
  4. dissolutionwas dissolved in 300 ml of water
  5. temperaturewhile cooling, saturated with sodium chloride
  6. extractionextracted three times with 1 1 of methylene chloride
  7. dry with materialThe organic extracts were dried over sodium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-672e250fc47843a9a8495173acf3d0c8
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

Loading…