hydrogenchloride in water T=110°C; 20 h;

jones reagent in acetone 1 h; Ambient temperatureother reagent, solvent, reaction time; Product distribution;

potassium hydroxide; hydrazine hydrate in various solvent(s) T=200°C; 6 h;

jones reagent in acetone T=20°C; Oxidation; 1 h;

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / |Inert atmosphere 1.2: 1 h / 0 - 20 °C / |Inert atmosphere 2.1: tetrahydrofuran; mineral oil / 5 h / 0 - 20 °C / |Inert atmosphere 3.1: tetrahydrofuran; mineral oil / |Reflux; |Inert atmosphere 4.1: tetrabutylammomium bromide; potassium permanganate; acetic acid / dichloromethane; water / 36 h / |Reflux 5.1: borane dimethyl sulfide complex / tetrahydrofuran / 12 h / 0 - 20 °C / |Inert atmosphere 5.2: 0.5 h / 0 °C 6.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / |Inert atmosphere 6.2: 1 h / 0 - 20 °C / |Inert atmosphere 7.1: tetrahydrofuran; mineral oil / 5 h / 0 - 20 °C / |Inert atmosphere 8.1: tetrahydrofuran; mineral oil / |Reflux; |Inert atmosphere 9.1: tetrabutylammomium bromide; potassium permanganate; acetic acid / dichloromethane; water / 36 h / |Reflux View Scheme

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / |Inert atmosphere 1.2: 1 h / 0 - 20 °C / |Inert atmosphere 2.1: tetrahydrofuran; mineral oil / 5 h / 0 - 20 °C / |Inert atmosphere 3.1: tetrahydrofuran; mineral oil / |Reflux; |Inert atmosphere 4.1: tetrabutylammomium bromide; potassium permanganate; acetic acid / dichloromethane; water / 36 h / |Reflux View Scheme

1.1: borane dimethyl sulfide complex / tetrahydrofuran / 12 h / 0 - 20 °C / |Inert atmosphere 1.2: 0.5 h / 0 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / |Inert atmosphere 2.2: 1 h / 0 - 20 °C / |Inert atmosphere 3.1: tetrahydrofuran; mineral oil / 5 h / 0 - 20 °C / |Inert atmosphere 4.1: tetrahydrofuran; mineral oil / |Reflux; |Inert atmosphere 5.1: tetrabutylammomium bromide; potassium permanganate; acetic acid / dichloromethane; water / 36 h / |Reflux View Scheme

1: 96 percent / Li2CuCl4 / tetrahydrofuran / -78 - 20 °C 2: 78 percent / PCC; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C 3: 70 percent / Jones reagent / acetone / 1 h / 20 °C View Scheme

1: 96 percent / Li2CuCl4 / tetrahydrofuran / -78 - 20 °C 2: 78 percent / PCC; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C 3: 70 percent / Jones reagent / acetone / 1 h / 20 °C View Scheme

2: 89 percent / KOH, NH2NH2*H2O / various solvent(s) / 6 h / 200 °C View Scheme