Hydrogen Peroxide → HCID 54296806, compound

HRID 1587700Notes

Reaction equation

HRID 1587700 reaction equation
[CH2:1]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[OH:18]O>C(O)(=O)C>[CH2:1]([C:12]1[CH:13]=[N+:14]([O-:18])[CH:15]=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 17967851HCID 17967851, compound

Product 1

HCID 54296806HCID 54296806, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 11.0 g (47 mmol) of 3-n-undecylpyridine and 8 ml of an aqueous 35% hydrogen peroxide dissolved in 30 ml of glacial acetic acid was heated at 70° to 80° C. for 3 hours, and then further heated with an additional 3 ml of hydrogen peroxide at the same temperature for 9 hours. After cooling, the mixture was concentrated under a reduced pressure to about a half amount, and 50 ml of water was added, followed by a concentration to a half amount (repeated twice). The residue was extracted with diethyl ether and washed with sodium hydrogen carbonate. After drying over anhydrous sodium sulfate, the product was concentrated under a reduced pressure, and the residue was purified by separation according to silica gel column chromatography (ethyl acetate→methanol:ethyl acetate=15:85) to obtain 10.2 g of the desired product (yield 86.8%).

Workup

  1. temperaturewas heated at 70° to 80° C. for 3 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated under a reduced pressure to about a half amount, and 50 ml of water
  4. additionwas added
  5. concentrationfollowed by a concentration to a half amount (
  6. extractionThe residue was extracted with diethyl ether
  7. washwashed with sodium hydrogen carbonate
  8. dry with materialAfter drying over anhydrous sodium sulfate
  9. concentrationthe product was concentrated under a reduced pressure
  10. customthe residue was purified by separation

Sources & evidence

ORD record
ord-e36eb240ca184054af79ba9e3166ddd3
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

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