1: 87 percent / K2CO3 / 2 h / Ambient temperature 2: 2.) aq. HCl / 1.) 60 deg C, 6 h, 2.) r.t., 12 h; 60 deg C, 30 min 3: 82 percent / H2 / Pd-C / diethyl ether View Scheme

1: H2 / Rh on Al2O3 2: CrO3 View Scheme

1: 2.) 10percent aq. HCl / 1.) diethyl ether, 1 h, heating 2: p-toluenesulfonic acid / toluene / Heating 3: H2 / 10percent Pd/C / ethanol 4: AlCl3 / 1,2-dichloro-ethane / 0.5 h 5: aq. NaOH, Br2 / dioxane / 3 h / 35 - 40 °C View Scheme

1: 2.) 10percent aq. HCl / 1.) diethyl ether, 1 h, heating 2: p-toluenesulfonic acid / toluene / Heating 3: H2 / 10percent Pd/C / ethanol 4: AlCl3 / 1,2-dichloro-ethane / 0.5 h 5: aq. NaOH, Br2 / dioxane / 3 h / 35 - 40 °C 6: SOCl2 / 1 h / Heating 7: 25percent aq. NH4OH 8: 64 percent / SOCl2, dimethylformamide / 1.5 h / Ambient temperature View Scheme

hydrogenchloride 1.) diethyl ether, 1 h, heating; Multistep reaction;

1: 2.) 10percent aq. HCl / 1.) diethyl ether, 1 h, heating 2: p-toluenesulfonic acid / toluene / Heating View Scheme