1: 77 percent / ammonium acetate / 0.5 h / Heating 2: 84 percent / LiAlH4, AlCl3 / diethyl ether / 1.5 h / Ambient temperature 3: 91 percent / triethylamine / diethyl ether / 3 h / Ambient temperature 4: 55 percent / polyphosphate ester / 9.5 h / 110 - 120 °C 5: 60 percent / decalin / 5 percent Pd/C / 3 h / 160 - 170 °C 6: 83 percent / Me2AlNH2 / benzene / 36 h / Heating 7: H2, conc. HCl / 5 percent Pd/C / methanol 8: 1,1-dichlorodimethyl ether / 0.5 h / 60 °C 9: 53 percent / 6 M HNO3; silver oxide / dioxane / 0.25 h / Ambient temperature View Scheme

1: 85 percent / NaOEt / ethanol / 7 h / -15 °C 2: toluene / 0.25 h / Ambient temperature 3: toluene / 0.5 h / Ambient temperature 4: toluene / 3 h / 160 °C 5: 40 percent / aq. LiOH / tetrahydrofuran / 12 h / Ambient temperature 6: 62 percent / diphenyl ether / 24 h / 180 °C 7: 50 percent / Ag2O, HNO3 / dioxane / 0.25 h / Ambient temperature View Scheme

1: NH4OAc / acetic acid 2: LiAlH4 / diethyl ether 3: BBr3 / CH2Cl2 View Scheme