Naphthalen-1(2H)-one → 2-Benzyl-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1585732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1585732
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH2:2]1.[H][H]>[Pd].C(OCC)(=O)C>[CH2:6]([CH:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]1=[O:11])[C:5]1[CH:10]=[CH:1][CH:2]=[CH:3][CH:4]=1

Komponenten

5

Edukt 2

HCID 12446728Naphthalen-1(2H)-oneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 5635332-Benzyl-1,2,3,4-tetrahydronaphthalen-1-oneAusbeute 114,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A Parr® hydrogenation bottle was charged with naphthalen-1-one (15 gm), ethyl acetate (150 mL) and 1 g of 10% palladium on charcoal. The mixture was hydrogenated on a Parr® shaker for about 15 hrs under 20 psi of hydrogen. The resulting mixture was filtered through a pad of Celite® and concentrated in vacuo to afford a red oil which was purified by flash chromatography (3:1 hexane/diethyl ether) to afford 14.1 gm of benzyltetralone, mp 50-51° C. Analysis calculated for C18H18O2 : 266.1302. Found: 266.1308.

Aufarbeitung

  1. filtrationThe resulting mixture was filtered through a pad of Celite®
  2. concentrationconcentrated in vacuo
  3. customto afford a red oil which
  4. customwas purified by flash chromatography (3:1 hexane/diethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-9ad32d60d28b4eaf9c596fd42321b093
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05939452

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