aluminium trichloride in water; ethyl acetate; toluene

in chlorobenzene

aluminium trichloride in chloroform a) RT, overnight, b) reflux, 1 h;

hydrogenchloride; water; iron in ethanol 1 h; Heating / reflux;

hydrogenchloride in ethanol; water; ethyl acetate

1: 70 percent / H2 / 5percent Pd/C / tetrahydrofuran / 25 °C / 2068.6 - 5171.5 Torr 2: 1.) conc. HCl, NaNO2, 2.) NaOAc / 1.) HOAc, H2O, 10 deg C, 30 min, 2.) HOAc, H2O, RT, 1 h 3: NaOAc / acetic acid; H2O / 2 h / 106 °C 4: 50percent H2SO4 / acetic acid; H2O / 2 h / Heating 5: 71 percent / mercaptoacetic acid / propionic acid / 1.3 h / 170 °C View Scheme