1: AlCl3 / dimethylformamide / 1 h / 90 °C 2: 85 percent / dimethylsulfoxide / 2 h / 80 °C 3: 95 percent / NH2NH2*H2O, KOH / bis-(2-hydroxy-ethyl) ether / 4 h / Heating 4: 95 percent / diethyl ether / 12 h / 0 °C 5: 90 percent / LiAlH4 / diethyl ether / 4 h / Heating 6: 88 percent / Me3SiI / CH2Cl2 / 24 h / Ambient temperature 7: 1.) n-BuLi / 1.) THF, -78 deg C, 60 min, 2.) THF, a) -78 deg C, 30 min, b) RT, 45 min 8: 89 percent / concd H2SO4 / 24 h / Heating 9: 95 percent / LiAlH4 / diethyl ether / 4 h / Heating 10: 85 percent / Me3SiI / CH2Cl2 / 24 h / Ambient temperature 11: 82 percent / dimethylsulfoxide / 2 h / 80 °C 12: 91 percent / KOH / ethane-1,2-diol / 6 h / Heating 13: 95 percent / diethyl ether / 12 h / 0 °C 14: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 15: 95 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme

1: 85 percent / dimethylsulfoxide / 2 h / 80 °C 2: 95 percent / NH2NH2*H2O, KOH / bis-(2-hydroxy-ethyl) ether / 4 h / Heating 3: 95 percent / diethyl ether / 12 h / 0 °C 4: 90 percent / LiAlH4 / diethyl ether / 4 h / Heating 5: 88 percent / Me3SiI / CH2Cl2 / 24 h / Ambient temperature 6: 1.) n-BuLi / 1.) THF, -78 deg C, 60 min, 2.) THF, a) -78 deg C, 30 min, b) RT, 45 min 7: 89 percent / concd H2SO4 / 24 h / Heating 8: 95 percent / LiAlH4 / diethyl ether / 4 h / Heating 9: 85 percent / Me3SiI / CH2Cl2 / 24 h / Ambient temperature 10: 82 percent / dimethylsulfoxide / 2 h / 80 °C 11: 91 percent / KOH / ethane-1,2-diol / 6 h / Heating 12: 95 percent / diethyl ether / 12 h / 0 °C 13: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 14: 95 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme

1: 65 percent / AlCl3 / nitrobenzene / 4.5 h / 0 - 20 °C 2: 96 percent / NH2NH2*H2O, KOH / bis-(2-hydroxy-ethyl) ether / 4 h / Heating 3: 77 percent / Ra-Ni, 10percent NaOH / 18 h / Heating 4: 95 percent / diethyl ether / 12 h / 0 °C 5: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 6: 95 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme

1: 91 percent / KOH / ethane-1,2-diol / 6 h / Heating 2: 95 percent / diethyl ether / 12 h / 0 °C 3: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 4: 95 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme

1: 82 percent / NH2NH2*H2O, KOH / bis-(2-hydroxy-ethyl) ether / 4 h / Heating 2: 65 percent / AlCl3 / nitrobenzene / 4.5 h / 0 - 20 °C 3: 96 percent / NH2NH2*H2O, KOH / bis-(2-hydroxy-ethyl) ether / 4 h / Heating 4: 77 percent / Ra-Ni, 10percent NaOH / 18 h / Heating 5: 95 percent / diethyl ether / 12 h / 0 °C 6: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 7: 95 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme

1: 82 percent / dimethylsulfoxide / 2 h / 80 °C 2: 91 percent / KOH / ethane-1,2-diol / 6 h / Heating 3: 95 percent / diethyl ether / 12 h / 0 °C 4: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 5: 95 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme

1: 1.)0.5N HCl, sodium nitrite / 1.)0-5 deg C, 5 min., 2.)H2O, 0-5 deg C, 20 min. 2: 53 percent / 1N NaOH / ethanol / 1 h / Heating 3: 65 percent / Trifluoroacetic acid, NaI / acetone / 1.)0-5 deg C, 2.)15 min., 25 deg C View Scheme