Hydrogen Peroxide → 4-Isopropyl-pyridine 1-oxide

HRID 2070923Notes

Reaction equation

HRID 2070923 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[OH:10]O.C(Cl)(Cl)Cl.O>CC(O)=O>[CH:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-:10])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 962WaterHCID 6212ChloroformHCID 696744-Isopropylpyridine

Product 1

HCID 3156064-Isopropyl-pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-isopropylpyridine and 1.5 mL of 30% H2O2 in 7 mL of AcOH was heated at 135° C. A total of 15.4 mL of H2O2 was added in 4 portions, and the solution was refluxed for 2 h. Chloroform and water were added, the layers were separated, and the aqueous layer was extracted 3 times with CHCl3. The combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (5% MeOH/CHCl3) provided 139 mg of the 4-isopropylpyridine N-oxide as an orange oil.

Workup

  1. temperaturethe solution was refluxed for 2 h
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted 3 times with CHCl3
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash silica gel chromatography (5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-bbcf805fa8e6471ab5c2a9504f342dd4
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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