(E)-3-[4-(1,1-dimethylethyl)phenyl]-2-propenoic acid phenylmethyl ester → 3-(4-Tert-butylphenyl)propanoic acid
Reaktionsgleichung
C1(C[O:8][C:9](=[O:22])/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=2)C=CC=CC=1>[Pd].CCO>[CH3:21][C:18]([C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][C:9]([OH:22])=[O:8])=[CH:17][CH:16]=1)([CH3:19])[CH3:20]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A stirring solution of (E)-3-[4-(1,1-dimethylethyl)phenyl]-2-propenoic acid phenylmethyl ester (2.04 g, 6.93 mmol) in 136 mL of abs. EtOH in the presence of 377 mg of 10% Pd/C was hydrogenated at room temperature at atmospheric pressure. After removing the catalyst by filtration through a pad of celite, the filtrate was concentrated to give 4-(1,1-dimethylethyl)benzenepropanoic acid, (1.39 g, 6.74 mmol) in 97% yield, m.p. 110°-113° C.