Hydrogen Peroxide → 4-(tert-Butyl)pyridine 1-Oxide
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureheated
- temperatureat reflux overnight
- customThe cooled mixture was evaporated to dryness
- dissolutionThe residue was dissolved in dichloromethane (200 ml)
- washwashed with brine (50 ml)
- dry with materialdried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-29a7064d6cf04d8ea08346aa4f2b6e70
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07285563B2
Reaction notes
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