Hydrogen Peroxide → 2-(5-Ethyl-1-oxidopyridin-1-ium-2-yl)ethanol

HRID 250158Notes

Reaction equation

HRID 250158 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][OH:11])=[N:7][CH:8]=1)[CH3:2].[OH:12]O>C(O)(=O)C>[CH3:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][OH:11])=[N+:7]([O-:12])[CH:8]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 788945-Ethyl-2-pyridineethanol

Product 1

HCID 668233992-(5-Ethyl-1-oxidopyridin-1-ium-2-yl)ethanolYield 81.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of 100 g (0.655 mol) 2-(5-ethyl-pyridin-2-yl)-ethanol in 500 mL acetic acid was added 118 g (1.049 mol) 30% hydrogen peroxide at 25-30° C. Reaction mixture was refluxed at 100° C. (tlc) for 14 hr. After completion of the reaction acetic acid was removed under vacuum, and the residual mass was poured in excess water and made alkaline by 10% Na2CO3 solution. Product was extracted with ethyl acetate and after concentrating ethyl acetate in vacuo, 89.58 g (81%) crystalline product was obtained.

Workup

  1. customReaction mixture
  2. customwas removed under vacuum
  3. additionthe residual mass was poured in excess water
  4. extractionProduct was extracted with ethyl acetate
  5. concentrationafter concentrating ethyl acetate in vacuo

Sources & evidence

ORD record
ord-25ce192bd4784c1e99536a44f56367a1
Source dataset
uspto-grants-2011_01
Patent number
US07863300B2

Reaction notes

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