1: LiAlH4 / diethyl ether / 0 °C 2: HBr / benzene / Heating 3: pyridinium p-toluenesulfonate / CH2Cl2 / 24 h / 20 °C View Scheme

1: 67 percent / 0.1 N Ba(OH)2 / methanol / 17 h 2: SOCl2 / 0.75 h / Heating View Scheme

1: LiAlH 2: 1.) 48 percent HBr, concd. H2SO4; 2.) KMnO4 / 1.) 3 h, reflux; 2.) 20percent H2SO4, 15-20 deg C View Scheme

1.1: LiAlH4 / diethyl ether / 0 °C 2.1: HBr / benzene / Heating 3.1: pyridinium p-toluenesulfonate / CH2Cl2 / 24 h / 20 °C 4.1: magnesium / tetrahydrofuran / 3 h / 55 °C 4.2: dilithium tetrachlorocuprate(II) / tetrahydrofuran / 3 h / 0 °C 5.1: 4.5 g / pyridinium p-toluenesulfonate / methanol / 3 h / Heating View Scheme

1: 99 percent / LiAlH4 / diethyl ether / 0.5 h 2: 73 percent / 48percent hydrobromic acid / benzene / 36 h / Heating 3: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 4: 1) magnesium, 2) Li2CuCl4 / 1) THF, 2) room temperature, 3 h 5: NaOH / ethanol / 2 h / Heating 6: 2 N HCl / ethanol / 1 h / Heating View Scheme

1: LiAlH 2: 1.) 48 percent HBr, concd. H2SO4; 2.) KMnO4 / 1.) 3 h, reflux; 2.) 20percent H2SO4, 15-20 deg C View Scheme

barium dihydroxide in methanol 17 h;