1: With sodium hydroxide; water T=20°C; 2 h; 2: With hydrogenchloride in water

sodium hydroxide in acetone 48 h; Heating; Yield given;

1: 100 percent / H2 / Pd/C / ethyl acetate; methanol / 5 h / 2068.59 Torr 2: K2CO3 / acetone; acetonitrile / 15 h / Heating 3: 1.26 g / KOH / methanol; H2O / 10 h / 70 °C View Scheme

1: K2CO3 / acetone; acetonitrile / 15 h / Heating 2: 1.26 g / KOH / methanol; H2O / 10 h / 70 °C View Scheme

sodium hydroxide; sodium amalgam T=70 - 80°C;

1: K2CO3 / acetone / 2 h / Heating 2: KOH / methanol / 38 °C View Scheme

1: K2CO3 / acetone / 2 h / Heating 2: KOH / methanol / 38 °C View Scheme

potassium hydroxide; potassium carbonate; sodium iodide 1) acetone, 8h, reflux; Yield given. Multistep reaction;

1.1: triethylamine / tetrahydrofuran / -70 - 0 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / -70 °C / Inert atmosphere 2.2: -70 - 0 °C / Inert atmosphere 3.1: potassium hexamethylsilazane / tetrahydrofuran; hexane / 1.17 h / -72 °C / Inert atmosphere 3.2: 2 h / -72 °C / Inert atmosphere 4.1: lithium borohydride / methanol; diethyl ether / 20 °C 5.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 20 °C 6.1: Fetizon's reagent (silver carbonate on celite) / benzene / 4 h / Reflux 7.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.25 h / -78 °C / Inert atmosphere 7.2: 22 h / -78 - -50 °C / Inert atmosphere 8.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 20 °C / 760.05 Torr / Inert atmosphere View Scheme

triethylammonium formate; palladium on activated charcoal 1 h; Ambient temperature;