15 wt palladium on carbon; hydrogen; acetic acid in ethanol T=35°C; P=3878.71 Torr; 18 h;

1: 1.) PPh3, DEAD / 1.) THF, 0 deg C, 5 min, 2.) THF, 0 deg C, 34 min 2: 16 percent / H2 / 10percent Pd/C / butan-1-ol View Scheme

1: With sulfuric acid in water 1 h; RefluxInert atmosphere; 2: With sodium carbonate in water Saturated solutionInert atmosphere;

1.1: n-butyllithium / diethyl ether; hexane / 0.33 h / -40 °C / Inert atmosphere 1.2: 1 h / -40 - 20 °C / Inert atmosphere 2.1: sulfuric acid / water / 1 h / Reflux; Inert atmosphere 2.2: Saturated solution; Inert atmosphere View Scheme