Ethanol → 3-(4-Amino-3-hydroxyphenyl)-acrylic acid ethyl ester

Participants

Reaction Steps

To a stirred suspension of 11-2 (4.64 g, 19.6 mmol), NH4Cl (524 mg, 9.8 mmol), EtOH (140 mL) and H2O (70 mL) was added iron dust (2.72 g, 48.9 mmol). The resulting yellow suspension was refluxed for 1.5 h., and then the solution was filtered while hot through celite. The filtrate was concentrated and the residue was partitioned between EtOAc and brine. The layers were separated and the EtOAc layer dried (Na2SO4) and concentrated to give 11-3 which was used without further purification in the next step.

Provenance & Evidence