1: 4-nitro-peroxybenzoic acid / 1,2-dichloro-ethane / Heating 2: Ph3P / 255 - 260 °C View Scheme

para-nitroperbenzoic acid in 1,2-dichloro-ethane Heating;

sodium nitrite in acetic acid

1.1: 66 percent / HNO3 / H2O / 0.08 h / -20 °C 2.1: 99 percent / NaBH4 / methanol / 0.17 h / 0 °C 3.1: 86 percent / TsOH / benzene / 16 h / Heating 4.1: O3 / CH2Cl2; methanol / -78 °C 4.2: Me2S; NaHCO3 / CH2Cl2; methanol / 4 h / 20 °C 4.3: 89 percent / NH3 / CH2Cl2; methanol; H2O / 16 h 5.1: 94 percent / NaOMe / dimethylformamide / 6 h / Heating 6.1: hydrazine monohydrate; Raney nickel / H2O; ethanol / 2 h / Heating 7.1: 34 percent / HOAc; NaNO2 / H2O / 0 - 20 °C View Scheme

T=400°C; 0.116667 h;

1.1: AlCl3 / CS2 / 16 h / 20 °C 2.1: 40.3 g / H2SO4 / H2O / 1 h / 80 °C 3.1: 66 percent / HNO3 / H2O / 0.08 h / -20 °C 4.1: 99 percent / NaBH4 / methanol / 0.17 h / 0 °C 5.1: 86 percent / TsOH / benzene / 16 h / Heating 6.1: O3 / CH2Cl2; methanol / -78 °C 6.2: Me2S; NaHCO3 / CH2Cl2; methanol / 4 h / 20 °C 6.3: 89 percent / NH3 / CH2Cl2; methanol; H2O / 16 h 7.1: 94 percent / NaOMe / dimethylformamide / 6 h / Heating 8.1: hydrazine monohydrate; Raney nickel / H2O; ethanol / 2 h / Heating 9.1: 34 percent / HOAc; NaNO2 / H2O / 0 - 20 °C View Scheme

1: 94 percent / NaOMe / dimethylformamide / 6 h / Heating 2: hydrazine monohydrate; Raney nickel / H2O; ethanol / 2 h / Heating 3: 34 percent / HOAc; NaNO2 / H2O / 0 - 20 °C View Scheme

1.1: 40.3 g / H2SO4 / H2O / 1 h / 80 °C 2.1: 66 percent / HNO3 / H2O / 0.08 h / -20 °C 3.1: 99 percent / NaBH4 / methanol / 0.17 h / 0 °C 4.1: 86 percent / TsOH / benzene / 16 h / Heating 5.1: O3 / CH2Cl2; methanol / -78 °C 5.2: Me2S; NaHCO3 / CH2Cl2; methanol / 4 h / 20 °C 5.3: 89 percent / NH3 / CH2Cl2; methanol; H2O / 16 h 6.1: 94 percent / NaOMe / dimethylformamide / 6 h / Heating 7.1: hydrazine monohydrate; Raney nickel / H2O; ethanol / 2 h / Heating 8.1: 34 percent / HOAc; NaNO2 / H2O / 0 - 20 °C View Scheme