Hydrogen Peroxide → 5-Phenyl-2-picoline N-oxide

HRID 1590091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1590091
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OO.CC[O:18]CC.CCOC(C)=O>CC(O)=O.[Pd]>[C:1]1([C:7]2[CH:12]=[N+:11]([O-:18])[C:10]([CH3:13])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 3

HCID 784Hydrogen PeroxideHCID 767442-Methyl-5-phenylpyridineHCID 21584169Diethylether ethylacetate

Produkt 1

HCID 149805285-Phenyl-2-picoline N-oxide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 100 g 5-phenyl-2-picoline in 170 mL of glacial HOAc was added 30% H2O2 and the resulting solution was heated at 70° C. overnight. After the reaction mixture was cooled to room temperature, 1 g of 10% Pd/C was added to destroy excess of H2O2. The reaction mixture was then filtered on celite, washed with toluene and the filtrate was evaporated to dryness affording a yellow solid residue. The crude material was swished with a mixture of Et2O/EtOAc (10:1) and filtered to afford the pure title product as a white solid, m.p.: 91° C.

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customto destroy excess of H2O2
  3. filtrationThe reaction mixture was then filtered on celite
  4. washwashed with toluene
  5. customthe filtrate was evaporated to dryness
  6. customaffording a yellow solid residue
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-9827f9b91e97460ca096e72a8cc2164b
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05202321

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