5-(Bicyclo[3.2.1]oct-2-ylidene)pentanoic acid → 5-(Bicyclo[3.2.1]oct-2-yl)pentanoic acid
Reaktionsgleichung
[CH:1]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][C:2]2=[CH:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].[H][H]>C(O)C.[Pt]=O>[CH:1]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH:2]2[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A solution of 3.4 g (16.3 mmol) of 5-(bicyclo[3.2.1]oct-2-ylidene)pentanoic acid in 100 ml of absolute ethanol was hydrogenated at 50 psi over 300 mg of platinum oxide in a Parr apparatus. After 1.5 hr hydrogen uptake became slow. After 4 hr the system was flushed with nitrogen, and the catalyst was removed by filtration through diatomaceous earth filter aid (Celite). The filtrate was evaporated in vacuo to yield 3.25 g (96%) of quite pure 5-(bicyclo[3.2.1]oct-2-yl)pentanoic acid as a colorless oil.