1: 9.5 g / K2CO3 / acetone / 3 h / Heating 2: LiCl / H2O; dimethylsulfoxide / 2 h / 165 °C 3: LiAlH4 / diethyl ether / 2 h / Heating 4: MnO2 / benzene / 12 h / Heating View Scheme

manganese(IV) oxide in benzene 12 h; Heating; Yield given;

1: 1.) DMAP, 2.) AlCl3 / 1.) CHCl3, reflux, 2.5 h, 2.) 1,2-dichloroethane, room temperature, 10 min 2: LiAlH4 / diethyl ether / 0.17 h / Heating 3: 5.2 g / K5IO6, aq. H2SO4 / ethanol / 1.) 0 deg C, 2 h, 2.) 0 deg C to room temperature 4: 9.5 g / K2CO3 / acetone / 3 h / Heating 5: LiCl / H2O; dimethylsulfoxide / 2 h / 165 °C 6: LiAlH4 / diethyl ether / 2 h / Heating 7: MnO2 / benzene / 12 h / Heating View Scheme

1: 5.2 g / K5IO6, aq. H2SO4 / ethanol / 1.) 0 deg C, 2 h, 2.) 0 deg C to room temperature 2: 9.5 g / K2CO3 / acetone / 3 h / Heating 3: LiCl / H2O; dimethylsulfoxide / 2 h / 165 °C 4: LiAlH4 / diethyl ether / 2 h / Heating 5: MnO2 / benzene / 12 h / Heating View Scheme

1: LiAlH4 / diethyl ether / 0.17 h / Heating 2: 5.2 g / K5IO6, aq. H2SO4 / ethanol / 1.) 0 deg C, 2 h, 2.) 0 deg C to room temperature 3: 9.5 g / K2CO3 / acetone / 3 h / Heating 4: LiCl / H2O; dimethylsulfoxide / 2 h / 165 °C 5: LiAlH4 / diethyl ether / 2 h / Heating 6: MnO2 / benzene / 12 h / Heating View Scheme

1: LiAlH4 / diethyl ether / 2 h / Heating 2: MnO2 / benzene / 12 h / Heating View Scheme