1: benzene; hydrogen bromide 2: benzene View Scheme

water

benzene

1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 1 h, 2.) from -78 deg C to RT 2: 94 percent / ethyl chloroformate / CHCl3 / 0.25 h / 0 °C 3: 88 percent / dimethylformamide / 4 h 4: concd H2SO4, H2 / PtO2 / ethanol / 12 h / 2585.7 Torr 5: benzene / 3 h / Heating 6: 93 percent / LiAlH4 / tetrahydrofuran / 5 h / Heating View Scheme

ammonium cerium(IV) nitrate; water in acetonitrile 2 h; Ambient temperature;

1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 1 h, 2.) from -78 deg C to RT 2: 94 percent / ethyl chloroformate / CHCl3 / 0.25 h / 0 °C 3: 88 percent / dimethylformamide / 4 h 4: concd H2SO4, H2 / PtO2 / ethanol / 12 h / 2585.7 Torr 5: benzene / 3 h / Heating 6: 93 percent / LiAlH4 / tetrahydrofuran / 5 h / Heating 7: 10 percent Spectr. / MnO2 / CH2Cl2 / 40 h / 23 °C View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 1 h, 2.) from -78 deg C to RT 2: 94 percent / ethyl chloroformate / CHCl3 / 0.25 h / 0 °C 3: 88 percent / dimethylformamide / 4 h 4: concd H2SO4, H2 / PtO2 / ethanol / 12 h / 2585.7 Torr 5: benzene / 3 h / Heating View Scheme

1: 1.) n-BuLi / 1.) ether, hexane, -78 deg C, 2.) ether, hexane, 2 h 2: NaHCO3, ethyl chloroformate / benzene / 1 h / Ambient temperature 3: benzene; dimethylformamide / 24 h View Scheme

hydrogen bromide; acetic acid 24 h; Heating;