1: 82 percent / H2 / 10percent Pd/C / ethyl acetate / 760 Torr 2: 1.) sodium nitrite, concd. H2SO4, 2.) cuprous chloride, concd. HCl / 1.) acetic acid, 0 deg C, 2.) acetic acid, a) from 5 deg C to RT, 1 h, b) 80 deg C, 30 min View Scheme

1: 82 percent / H2 / 10percent Pd/C / ethyl acetate / 760 Torr 2: 1.) sodium nitrite, concd. H2SO4, 2.) cuprous chloride, concd. HCl / 1.) acetic acid, 0 deg C, 2.) acetic acid, a) from 5 deg C to RT, 1 h, b) 80 deg C, 30 min 3: thionyl chloride / 2 h / 100 °C 4: diethyl ether / Ambient temperature 5: AgNO3, NH4OH / dioxane / 16 h / Heating 6: aq. NaOH / 2-ethoxy-ethanol / 16 h / Heating View Scheme