1: 58 percent / trifluoroacetic acid / 3 h / Heating 2: 77 percent / ammonium acetate / 0.5 h / Heating 3: 84 percent / LiAlH4, AlCl3 / diethyl ether / 1.5 h / Ambient temperature 4: 91 percent / triethylamine / diethyl ether / 3 h / Ambient temperature 5: 55 percent / polyphosphate ester / 9.5 h / 110 - 120 °C 6: 60 percent / decalin / 5 percent Pd/C / 3 h / 160 - 170 °C 7: 83 percent / Me2AlNH2 / benzene / 36 h / Heating 8: H2, conc. HCl / 5 percent Pd/C / methanol 9: 1,1-dichlorodimethyl ether / 0.5 h / 60 °C 10: 53 percent / 6 M HNO3; silver oxide / dioxane / 0.25 h / Ambient temperature View Scheme

nitric acid 0.0833333 h; Ambient temperature;

1: (i) AlCl3, benzene, (ii) HCl 2: NH4OAc / acetic acid 3: LiAlH4 / diethyl ether 4: BBr3 / CH2Cl2 View Scheme