4-[1-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzoic acid → 4-[1-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl]-benzoic acid

HRID 356727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 356727
[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)=[CH2:15])[CH:5]=[CH:4][C:3]1=2.[H][H]>[Pd].C(O)C>[CH3:25][C:2]1([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH:14]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)[CH3:15])[CH:5]=[CH:4][C:3]1=2

Komponenten

5

Edukt 2

HCID 99057294-[1-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzoic acidHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 103149774-[1-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl]-benzoic acidAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

The olefin 48 (0.0105 g, 0.0314 mmol) was hydrogenated over 5% palladium on charcoal (1 mg) in 0.5 mL of ethanol at room temperature and atmospheric pressure. After one equivalent (0.7 mL) of hydrogen was taken up, the catalyst was removed by filtration through a small Celite pad. The solvent was removed in vacuo to give the crude acid as a white solid (0.019 g). Recrystallization from benzene-hexane afforded the desired acid 49 as a white crystalline solid (0.0078 g, 74%): m.p. 186°-188° C. The structure of the product was also confirmed using IR, 1H NMR and mass spectroscopy.

Aufarbeitung

  1. customthe catalyst was removed by filtration through a small Celite pad
  2. customThe solvent was removed in vacuo
  3. customto give the crude acid as a white solid (0.019 g)
  4. customRecrystallization from benzene-hexane

Quellen und Nachweise

ORD-Eintrag
ord-d4e4b014482149fdbbce1c762864514e
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05837725

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