1: hydrogen / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 2: 1.) NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, water, 5 deg C, 30 min, 2.) acetone, water, 35 deg C View Scheme

1: hydrogen / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 2: 1.) NaNO2, 47percent HBr, 2.) Cu2O / 1.) acetone, water, 5 deg C, 30 min, 2.) acetone, water, 35 deg C 3: 2.) 2N HCl / 1.) sulfolane, 110 deg C, 2 h; 2.) sulfolane, reflux, 8 h View Scheme

sodium hydride in dimethyl sulfoxide T=70°C; 0.5 h;

hydrogen; palladium on activated charcoal in methanol P=760 Torr; Ambient temperature;