Acetovanillone → 4-Ethylguaiacol

HRID 55604

Reaktionsgleichung

Reaktionsgleichung von HRID 55604
[CH3:1][C:2]([C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1)=O>C(O)C.[Pd].Cl>[CH2:2]([C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1)[CH3:1]

Komponenten

5

Edukt 1

HCID 2214Acetovanillone

Produkt 1

HCID 624654-EthylguaiacolAusbeute 102,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Acetovanillone (Aldrich, 11.0 g, 66 mmol) was dissolved in absolute ethanol (200 ml) and added to 1.5 g of 5% palladium on carbon. A few drops of concentrated hydrochloric acid were added and the mixture hydrogenated on a shaker at 42 psi. The reaction mixture was filtered through Celite, and the filtrate was concentrated to afford 10.3 g of a golden liquid. This was diluted with water, extracted with diethyl ether and the organic phase was washed with water and sodium bicarbonate. The solvent was dried (MgSO4) and concentrated to afford 9.3 g of a slightly yellow liquid.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-3151ed57c0d4466eaf2c0aade4f7d137
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624927

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