sodium in pentan-1-ol; toluene 0.25 h; RefluxInert atmosphere; Overall yield = 95 percent; Overall yield = 18 g;

hydrogen; platinum(IV) oxide in ethanol; acetic acid P=2316.8 Torr; 48 h;

sodium in pentan-1-ol; toluene 0.25 h; RefluxInert atmosphere; Overall yield = 95 percent; Overall yield = 18 g;

1: sodium; pentan-1-ol / 2 h / Reflux 2: triethylamine / dichloromethane / 12 h / Reflux 3: ammonium formate / palladium 10 on activated carbon / methanol / 12 h / Reflux View Scheme

sodium in pentan-1-ol 4 h; Heating / reflux;

1: sodium; propan-1-ol / toluene / 12 h / |Reflux; |Inert atmosphere 2: tetrahydrofuran / 72 h / 20 °C / |Inert atmosphere 3: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C / |Inert atmosphere 4: sodium carbonate / water; dichloromethane / 0 - 20 °C / |Inert atmosphere 5: phosphorus pentachloride / dichloromethane / 2 h / 0 - 20 °C / |Inert atmosphere 6: dichloromethane; 1,1-dimethylpropan-1-ol / 0 - 20 °C / |Inert atmosphere 7: acetic acid / ethyl acetate / 0.5 h / 80 °C / |Inert atmosphere 8: palladium 10 on activated carbon; hydrogen / methanol / 20 °C / 2585.81 Torr / |Inert atmosphere View Scheme