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
Conditions
- Temperature
- 90 °C
Procedure
In a round-bottomed flask, 4-tert-butylpyridine (1.5 g, 11.1 mmol) was dissolved in acetic acid (9 mL) and hydrogen peroxide (30 wt. % solution in water, 6.0 mL, 58.7 mmol) was added. The colorless solution was stirred at 90° C. overnight. The reaction mixture was cooled to room temperature and concentrated. The residue was poured onto ˜40 mL saturated Na2CO3 solution and extracted with 100 mL dichloromethane (2×). The organic layers were combined, dried over sodium sulfate, filtered and concentrated to afford 1.75 g (99%) of 4-tert-butylpyridine N-oxide as light yellow solid.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- concentrationconcentrated
- additionThe residue was poured onto ˜40 mL saturated Na2CO3 solution
- extractionextracted with 100 mL dichloromethane (2×)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2e129aef61bf4860a4b105426baa15bb
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518945B2
Reaction notes
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