Ethyl-12-(m-nitrophenyl)-11-dodecenoate → Ethyl-12-(m-aminophenyl)-dodecanoate

Participants

Reaction Steps

Ethyl-12-(m-nitrophenyl)-11-dodecenoate (9.76 g, 28.1 mmol was dissolved in ethyl acetate (55 ml). The solution was hydrogenated over 5% Pd/C (0.346 g) at room temperature and at an initial pressure of 45 psi for four hours. The reaction mixture was filtered through Celite and the solvent was removed under reduced pressure to yield an oily residue. The crude product was purified by column chromatography (80 g silica gel, hexanes:ethyl acetate, discontinuous gradient 10:1-2:1) to yield the reduced compound 5, ethyl-12-(m-aminophenyl)-dodecanoate (8.75 g, 97.5% yield).

Provenance & Evidence