hydrogen; palladium on activated charcoal in ethanol; ethyl acetate P=760 Torr; 15 h; Ambient temperature;

1: 71 percent / LiBr, toluene-4-sulfonic acid hydrate / 15 h / Ambient temperature 2: 36 percent / AlCl3 / CH2Cl2 / 1 h / 3 - 4 °C 3: 95 percent / hydrogen / 5percent Pd/C / ethyl acetate; ethanol / 15 h / 760 Torr / Ambient temperature View Scheme

1: 36 percent / AlCl3 / CH2Cl2 / 1 h / 3 - 4 °C 2: 95 percent / hydrogen / 5percent Pd/C / ethyl acetate; ethanol / 15 h / 760 Torr / Ambient temperature View Scheme

1: glacial acetic acid; HBr / 100 °C 2: ethanol 3: potassium hydroxide; amyl alcohol View Scheme

pyridinium chlorochromate in dichloromethane 15 h; Ambient temperature;