Hydrogen Peroxide → HCID 22677030, compound

HRID 1857300Notes

Reaction equation

HRID 1857300 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21]B(O)O)=[CH:17][N:16]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].OO.CO>C1COCC1>[OH:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:13]=[CH:14][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:10][CH:11]=2)=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 22129303HCID 22129303, compound

Product 1

HCID 22677030HCID 22677030, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Octylphenyl)pyridin-5-yl-boric acid (10 g) was mixed with 20 ml of aqueous hydrogen peroxide (36%), methanol (80 ml) and THF (80 ml) to stand overnight under gentle agitation at room temperature. Organic matter in the reaction mixture was extracted by diethyl ether (200 ml), followed by washing the extract sequentially with saturated aqueous sodium hydrogen sulfite, distilled water and aqueous ammonium chloride to be dried over MgSO4. This extract mixture was concentrated by distilling off the solvent to obtain solid product, which was purified by recrystallization from mixed solvent of heptane and ethyl acetate to give 5-hydroxy-2-(4-octylphenyl)pyridine (5.8 g). The melting point of this product was found to be 134-135.5° C.

Workup

  1. extractionOrganic matter in the reaction mixture was extracted by diethyl ether (200 ml)
  2. washby washing the
  3. extractionextract sequentially with saturated aqueous sodium hydrogen sulfite
  4. distillationdistilled water and aqueous ammonium chloride
  5. dry with materialto be dried over MgSO4
  6. concentrationThis extract mixture was concentrated
  7. distillationby distilling off the solvent
  8. customto obtain solid product, which
  9. customwas purified by recrystallization
  10. additionfrom mixed solvent of heptane and ethyl acetate

Sources & evidence

ORD record
ord-2ef4546619a14378b47314d998cb6830
Source dataset
uspto-grants-2000_11
Patent number
US06146547

Reaction notes

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