1: 84 percent / LiAlH4, AlCl3 / diethyl ether / 1.5 h / Ambient temperature 2: 91 percent / triethylamine / diethyl ether / 3 h / Ambient temperature 3: 55 percent / polyphosphate ester / 9.5 h / 110 - 120 °C 4: 60 percent / decalin / 5 percent Pd/C / 3 h / 160 - 170 °C 5: 83 percent / Me2AlNH2 / benzene / 36 h / Heating 6: H2, conc. HCl / 5 percent Pd/C / methanol 7: 1,1-dichlorodimethyl ether / 0.5 h / 60 °C 8: 53 percent / 6 M HNO3; silver oxide / dioxane / 0.25 h / Ambient temperature View Scheme

1: LiAlH4 / diethyl ether 2: BBr3 / CH2Cl2 View Scheme