Hydrogen Peroxide → 2,5-Dimethylpyridin-1-ium-1-olate

HRID 868976Notes

Reaction equation

HRID 868976 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[OH:9]O>C(O)(=O)C.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N+:3]=1[O-:9]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 115262,5-Dimethylpyridine

Product 1

HCID 5717732,5-Dimethylpyridin-1-ium-1-olate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,5-dimethylpyridine (12.5 g, 0.12 mol) and 30% hydrogen peroxide (30 mL) in acetic acid (25 mL) was stirred at 90° C. for 48 h. The reaction mixture was diluted with water (50 mL) and concentrated to a volume of approximately 25 mL. The concentrated solution was neutralized with solid sodium carbonate, extracted with DCM (100 mL×3), dried with anhydrous sodium sulfate, and concentrated to give 14.4 g of the product as a yellow oil. MS (ESI): m/z 124.1 [M+H]+.

Workup

  1. concentrationconcentrated to a volume of approximately 25 mL
  2. extractionextracted with DCM (100 mL×3)
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fc397ec1e8f241b290b4fb4744452eb4
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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