Reaction #665229

Reaction equation

sodium sulfite

sodium carbonate

2,3,5-trimethylpyridine

acetic acid

hydrogen peroxide water

→

title compound

Yield 94.5%

2,3,5-trimethylpyridine 1-oxide

Yield 94.5%

Solvents

water

Conditions

Workup

1. 1
   workup.ADDITIONThis reaction mixed solution
2. 2
   Extractionthe resultant mixture was extracted with chloroform (3.0 L×4)
3. 3
   ConcentrationThe resultant organic layer was concentrated until crystals
4. 4
   Otherprecipitated
5. 5
   workup.ADDITIONThe precipitate was charged with n-hexane (2.5 L)
6. 6
   FiltrationThe obtained crystals were filtered

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.

Source