sodium hydroxide in methanol T=20°C;

1: NBS, benzoylperoxide / CCl4 / 5 h / Heating 2: 35 percent / 0.2 N NaOH / methanol / 20 °C View Scheme

hydrogen; platinum(IV) oxide in methanol T=25°C; P=735.5 Torr; 20 h;

1: 95 percent / H2 / PtO2, 80percent / methanol / 20 h / 25 °C / 735.5 Torr 2: 64 percent / 2,6-lutidine / benzene 3: 78 percent / NaH / dimethylformamide; CH2Cl2 / Ambient temperature View Scheme

1: 95 percent / H2 / PtO2, 80percent / methanol / 20 h / 25 °C / 735.5 Torr 2: 64 percent / 2,6-lutidine / benzene 3: 78 percent / NaH / dimethylformamide; CH2Cl2 / Ambient temperature 4: 90 percent / water, NaOH / pyridine; methanol / 24 h / Heating View Scheme

1: 95 percent / H2 / PtO2, 80percent / methanol / 20 h / 25 °C / 735.5 Torr 2: 64 percent / 2,6-lutidine / benzene 3: 78 percent / NaH / dimethylformamide; CH2Cl2 / Ambient temperature 4: 90 percent / water, NaOH / pyridine; methanol / 24 h / Heating 5: 48 percent / BBr3 / CH2Cl2 / 24 h / -35 °C View Scheme