4-(2-Acetamidoethyl)benzoic acid → N-{2-[4-(Hydroxymethyl)phenyl]ethyl}acetamide
Reaktionsgleichung
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>>[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][OH:12])=[CH:14][CH:15]=1)(=[O:3])[CH3:2]Komponenten
3
Versuchsvorschrift
4-(2-Acetamidoethyl)-benzoic acid is reduced, via a mixed anhydride, with sodium borohydride to give 4-(2-acetamidoethyl)-benzyl alcohol (m.p. 72°-73° C.) and then oxidized with activated manganese dioxide to give 4-(2-acetamidoethyl)-benzaldehyde (m.p. 81°-83° C.). Subsequent reaction with malonic acid gives 4-(2-acetamidoethyl)-cinnamic acid (m.p. 206°-208° C.), which is hydrogenated to give β-[4-(2-acetamidoethyl)-phenyl]-propionic acid (m.p. 132°-133° C.). This is then subjected to acidic saponification and reacted directly with ethanol to give ethyl β-[4-(2-aminoethyl)-phenyl]-propionate hydrochloride (m.p. 165°-167° C.).
Quellen und Nachweise
- ORD-Eintrag
- ord-30f9ba0e2e5240c8bb89b8d779faa7f5