Acetic Acid → 2,3,5-Trimethyl-1-oxidopyridin-1-ium

HRID 31720

Reaction equation

HRID 31720 reaction equation
C(O)(=[O:3])C.[CH3:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][N:7]=1.OO.S([O-])([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][N+:7]=1[O-:3]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 127592,3,5-TrimethylpyridineHCID 24437Sodium Sulfite

Product 1

HCID 104869072,3,5-Trimethyl-1-oxidopyridin-1-iumYield 94.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To acetic acid (1.43 kg, 23.83 mol), 2,3,5-trimethylpyridine (1.43 kg, 11.80 mol) was added over 15 minutes. After 15 minutes, a 35% hydrogen peroxide solution (1.38 kg, 14.2 mol) was added dropwise over 30 minutes, the mixture was stirred at 90° C. to 95° C. overnight. To the reaction mixture, sodium sulfite (220 g) was added. The reaction mixture was poured into a mixture of sodium carbonate (2.5 kg) and water (12 L) and the mixture was extracted with chloroform (3.0 L×4). The organic layer obtained was concentrated until crystal precipitated. To the precipitate, n-hexane (2.5 L) was added. The resultant mixture was stirred under ice-cool overnight The resultant solid was filtrated to obtain a desired compound (1.53 kg).

Workup

  1. extractionthe mixture was extracted with chloroform (3.0 L×4)
  2. customThe organic layer obtained
  3. concentrationwas concentrated until crystal
  4. customprecipitated
  5. additionTo the precipitate, n-hexane (2.5 L) was added
  6. stirringThe resultant mixture was stirred under ice-
  7. temperaturecool overnight The resultant solid
  8. filtrationwas filtrated

Sources & evidence

ORD record
ord-835a3f9320ec4f6fbf1a220927959d79
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

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