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

HRID 578047Notes

Reaction equation

HRID 578047 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][N:3]=1.C(O)(=[O:12])C.O.OO.S([O-])([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][N+:3]=1[O-:12]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 127592,3,5-TrimethylpyridineHCID 24437Sodium SulfiteHCID 449047Hydrogen peroxide water

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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

Workup

  1. additionThis reaction mixed solution
  2. extractionthe resultant mixture was extracted with chloroform (3.0 L×4)
  3. concentrationThe resultant organic layer was concentrated until crystals
  4. customprecipitated
  5. additionThe precipitate was charged with n-hexane (2.5 L)
  6. filtrationThe obtained crystals were filtered

Sources & evidence

ORD record
ord-65924572eabb4195866c3a9cf9226dbb
Source dataset
uspto-grants-2015_05
Patent number
US09040564B2

Reaction notes

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