1: HCl / diethyl ether 2: xylene / 3 h / 140 °C 3: 30 percent / PdCl2 / nitrobenzene / 2 h / 140 °C 4: 87 percent / Pd/C 5 percent / various solvent(s) / 3 h / Heating 5: 46 percent / POCl3 / various solvent(s) / 5 h / Heating 6: 82.7 percent / 2 h / 100 °C 7: 74.6 percent / H2 / Raney nickel / ethanol / 24 h / 20 °C / 6080 Torr 8: 92 percent / pyridine / 72 h / 20 °C 9: 80 percent / HCl / dioxane / 6.5 h View Scheme

1: HCl / diethyl ether 2: xylene / 3 h / 140 °C 3: 30 percent / PdCl2 / nitrobenzene / 2 h / 140 °C View Scheme

1: HCl / diethyl ether 2: xylene / 3 h / 140 °C 3: 30 percent / PdCl2 / nitrobenzene / 2 h / 140 °C 4: 87 percent / Pd/C 5 percent / various solvent(s) / 3 h / Heating View Scheme

1: HCl / diethyl ether 2: xylene / 3 h / 140 °C 3: 30 percent / PdCl2 / nitrobenzene / 2 h / 140 °C 4: 87 percent / Pd/C 5 percent / various solvent(s) / 3 h / Heating 5: 46 percent / POCl3 / various solvent(s) / 5 h / Heating 6: 82.7 percent / 2 h / 100 °C 7: 74.6 percent / H2 / Raney nickel / ethanol / 24 h / 20 °C / 6080 Torr View Scheme

With  hydrogenchloride in  xylene T=140°C; 3 h;  other Lewis and Bronsted acids as catalyst, var. time, var. temperature;  Product distribution;