Hydrogen Peroxide → 4-(tert-Butyl)pyridine 1-Oxide

HRID 1181384Notes

Reaction equation

HRID 1181384 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH:11]O>C(O)(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][N+:8]([O-:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 198784-tert-Butylpyridine

Product 1

HCID 1410394-(tert-Butyl)pyridine 1-OxideYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-tert-butylpyridine (44.3 ml, 300 mmol) in glacial acetic acid (200 ml) was added hydrogen peroxide (37.1 ml of a 27.5% aqueous solution, 300 mmol), and the resulting mixture heated at reflux overnight. The cooled mixture was evaporated to dryness. The residue was dissolved in dichloromethane (200 ml), and washed with brine (50 ml), then dried (Na2SO4) and evaporated to give the title compound (40 g, 88%) as a white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe cooled mixture was evaporated to dryness
  4. dissolutionThe residue was dissolved in dichloromethane (200 ml)
  5. washwashed with brine (50 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-29a7064d6cf04d8ea08346aa4f2b6e70
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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