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

HRID 1506272Notes

Reaction equation

HRID 1506272 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 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Conditions

Temperature
80 °C

Procedure

In a reaction flask, 4-(tert-butyl)pyridine (13.5 g, 99.8 mmol) was dissolved in 70 ml of acetic acid (1.29 mmol), and 30 ml of hydrogen peroxide (H2O2) (30%, 0.30 mol) was then slowly added to obtain a mixture. The mixture was heated to 80° C. for reaction for 24 hours, and the temperature was then slowly reduced to 20° C. The reaction flask was vacuum pumped to remove solvents from the mixture, followed by addition of a sodium hydroxide aqueous solution to adjust the pH of the mixture to 8. Next, the mixture was washed several times with dichloromethane and with deionized water to collect an organic layer, and the organic layer was dehydrated using sodium sulfate (Na2SO4). The solvent was then removed from the organic layer, followed by vacuum drying, thereby obtaining light yellow solids (13 g, 87% yield), which was Compound L4-1 having a chemical structure represented by

Workup

  1. customto obtain a mixture
  2. customwas then slowly reduced to 20° C
  3. customto remove solvents from the mixture
  4. additionfollowed by addition of a sodium hydroxide aqueous solution
  5. washNext, the mixture was washed several times with dichloromethane
  6. customwith deionized water to collect an organic layer
  7. customThe solvent was then removed from the organic layer
  8. customdrying

Sources & evidence

ORD record
ord-5251ba51da4d45d98fc84c7f354bed93
Source dataset
uspto-grants-2015_12
Patent number
US09219237B1

Reaction notes

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