sodium hydride in dimethyl sulfoxide T=80°C; 24 h;

1: 60 percent / KMnO4 2: 73 percent / Ra-Ni / 250 °C 3: 92 percent / H2SO4 / benzene 4: 95 percent / LiAlH4 / diethyl ether / 3 h / Heating 5: 88 percent / 48 percent HBr / 1 h / 50 °C 6: 93 percent / xylene / 2 h / Heating 7: 77 percent / NaH / dimethylsulfoxide / 24 h / 80 °C View Scheme

1: 73 percent / Ra-Ni / 250 °C 2: 92 percent / H2SO4 / benzene 3: 95 percent / LiAlH4 / diethyl ether / 3 h / Heating 4: 88 percent / 48 percent HBr / 1 h / 50 °C 5: 93 percent / xylene / 2 h / Heating 6: 77 percent / NaH / dimethylsulfoxide / 24 h / 80 °C View Scheme

1: 92 percent / sodium bichromate 2: 60 percent / KMnO4 3: 73 percent / Ra-Ni / 250 °C 4: 92 percent / H2SO4 / benzene 5: 95 percent / LiAlH4 / diethyl ether / 3 h / Heating 6: 88 percent / 48 percent HBr / 1 h / 50 °C 7: 93 percent / xylene / 2 h / Heating 8: 77 percent / NaH / dimethylsulfoxide / 24 h / 80 °C View Scheme

1: 93 percent / xylene / 2 h / Heating 2: 77 percent / NaH / dimethylsulfoxide / 24 h / 80 °C View Scheme

1: 88 percent / 48 percent HBr / 1 h / 50 °C 2: 93 percent / xylene / 2 h / Heating 3: 77 percent / NaH / dimethylsulfoxide / 24 h / 80 °C View Scheme

1: 95 percent / LiAlH4 / diethyl ether / 3 h / Heating 2: 88 percent / 48 percent HBr / 1 h / 50 °C 3: 93 percent / xylene / 2 h / Heating 4: 77 percent / NaH / dimethylsulfoxide / 24 h / 80 °C View Scheme