1: With water; sodium hydroxide T=40°C; Darkness; 2: With acetic acid in water Darkness;

sulfuric acid in water T=80°C; 0.166667 h;

palladium on activated charcoal; hydrogen

1: 65 percent / KOH, KCl, 27percent H2O2 / 20 °C 2: 1.) concd. H2SO4, NaNO2, 2.) KI / 1.) water, 10 deg C, 2.) 100 deg C 3: 63 percent / tris<2-(2-methoxyethoxy)ethyl>amine (TDA-1), CuCl / dimethylsulfoxide / 12 h / 95 °C 4: 70 percent / concd. H2SO4 / H2O / 0.17 h / 80 °C View Scheme

1: 65 percent / CH3SO3H / 70 - 80 °C 2: 65 percent / KOH, KCl, 27percent H2O2 / 20 °C 3: 1.) concd. H2SO4, NaNO2, 2.) KI / 1.) water, 10 deg C, 2.) 100 deg C 4: 63 percent / tris<2-(2-methoxyethoxy)ethyl>amine (TDA-1), CuCl / dimethylsulfoxide / 12 h / 95 °C 5: 70 percent / concd. H2SO4 / H2O / 0.17 h / 80 °C View Scheme

1: 1.) concd. H2SO4, NaNO2, 2.) KI / 1.) water, 10 deg C, 2.) 100 deg C 2: 63 percent / tris<2-(2-methoxyethoxy)ethyl>amine (TDA-1), CuCl / dimethylsulfoxide / 12 h / 95 °C 3: 70 percent / concd. H2SO4 / H2O / 0.17 h / 80 °C View Scheme

1: 63 percent / tris<2-(2-methoxyethoxy)ethyl>amine (TDA-1), CuCl / dimethylsulfoxide / 12 h / 95 °C 2: 70 percent / concd. H2SO4 / H2O / 0.17 h / 80 °C View Scheme

1: Na2SO4, hydroxylamine sulfate, concd. HCl / H2O 2: 65 percent / CH3SO3H / 70 - 80 °C 3: 65 percent / KOH, KCl, 27percent H2O2 / 20 °C 4: 1.) concd. H2SO4, NaNO2, 2.) KI / 1.) water, 10 deg C, 2.) 100 deg C 5: 63 percent / tris<2-(2-methoxyethoxy)ethyl>amine (TDA-1), CuCl / dimethylsulfoxide / 12 h / 95 °C 6: 70 percent / concd. H2SO4 / H2O / 0.17 h / 80 °C View Scheme

1: 71 percent / tris[2-(2-methoxyethoxy)ethyl]amine; CuCl / dimethylformamide / 4 h / 85 °C 2: 87 g / H2SO4 / H2O / 0.92 h / 90 °C View Scheme