sodium hydroxide in ethanol 1.5 h; Heating;

1: SOCl2 / dimethylformamide / 1 h / 80 °C 2: AlCl3 / dimethylformamide / 1 h / 90 °C 3: 85 percent / dimethylsulfoxide / 2 h / 80 °C 4: 95 percent / NH2NH2*H2O, KOH / bis-(2-hydroxy-ethyl) ether / 4 h / Heating 5: 95 percent / diethyl ether / 12 h / 0 °C 6: 90 percent / LiAlH4 / diethyl ether / 4 h / Heating 7: 88 percent / Me3SiI / CH2Cl2 / 24 h / Ambient temperature 8: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 10 min, b) from -78 deg C to RT 9: 86 percent / concd H2SO4 / 24 h / Heating 10: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 11: 90 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme

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, 2.) THF, a) -78 deg C, 10 min, b) from -78 deg C to RT 8: 86 percent / concd H2SO4 / 24 h / Heating 9: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 10: 90 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, 2.) THF, a) -78 deg C, 10 min, b) from -78 deg C to RT 7: 86 percent / concd H2SO4 / 24 h / Heating 8: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 9: 90 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme

1: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 2: 90 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme

1: 86 percent / concd H2SO4 / 24 h / Heating 2: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 3: 90 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme