hydrogen; palladium on activated charcoal in methanol P=760 Torr;

lithium aluminium tetrahydride in tetrahydrofuran 24 h; Heating;

1: 33 percent / NaH / tetrahydrofuran / 18 h / 65 °C 2: 85 percent / H2 / Pd-C / methanol / 760 Torr View Scheme

potassium tert-butylate in 1,4-dioxane; tert-butyl alcohol 2 h;

1.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / dichloromethane; water / 6.5 h 2.1: sodium hydroxide; tetrabutylammomium bromide; caesium chloride / water; benzene / 15 h / 70 °C 3.1: hydrogen; palladium 10 on activated carbon; acetic acid / methanol / 4 - 5 h 3.2: pH 9 - 10 View Scheme