1: activated Fe / acetic acid; H2O / 0.75 h / 85 - 90 °C 2: 78 percent / trifluoroacetic acid / 0.5 h / 4 °C 3: 96 percent / K2CO3 / 1,2-dimethoxy-ethane / 24 h / Ambient temperature 4: 1.) 90percent fuming HNO3, CF3SO3H, 2.) aq. 0.2 M K2CO3 / 1.) -20 deg C, 2 h, 2.) ethanol, RT, 15 h 5: 1.) activated Fe, 2.) water / 1.) benzene, reflux, 30 min, 2.) benzene, reflux 6: 1 N aq. HCl / 1.25 h / 75 °C View Scheme

1: 96 percent / K2CO3 / 1,2-dimethoxy-ethane / 24 h / Ambient temperature 2: 1.) 90percent fuming HNO3, CF3SO3H, 2.) aq. 0.2 M K2CO3 / 1.) -20 deg C, 2 h, 2.) ethanol, RT, 15 h 3: 1.) activated Fe, 2.) water / 1.) benzene, reflux, 30 min, 2.) benzene, reflux 4: 1 N aq. HCl / 1.25 h / 75 °C View Scheme

1: 78 percent / trifluoroacetic acid / 0.5 h / 4 °C 2: 96 percent / K2CO3 / 1,2-dimethoxy-ethane / 24 h / Ambient temperature 3: 1.) 90percent fuming HNO3, CF3SO3H, 2.) aq. 0.2 M K2CO3 / 1.) -20 deg C, 2 h, 2.) ethanol, RT, 15 h 4: 1.) activated Fe, 2.) water / 1.) benzene, reflux, 30 min, 2.) benzene, reflux 5: 1 N aq. HCl / 1.25 h / 75 °C View Scheme

hydrogenchloride T=75°C; 1.25 h; Yield given;

1: 1.) activated Fe, 2.) water / 1.) benzene, reflux, 30 min, 2.) benzene, reflux 2: 1 N aq. HCl / 1.25 h / 75 °C View Scheme

1: 1.) 90percent fuming HNO3, CF3SO3H, 2.) aq. 0.2 M K2CO3 / 1.) -20 deg C, 2 h, 2.) ethanol, RT, 15 h 2: 1.) activated Fe, 2.) water / 1.) benzene, reflux, 30 min, 2.) benzene, reflux 3: 1 N aq. HCl / 1.25 h / 75 °C View Scheme