sodium hydroxide in dimethyl sulfoxide

1: 79 percent / unfused ZnCl2 with 5percent water, POCl3 / 5 h / 50 °C 2: 80 percent / K2CO3, KI / dimethylformamide / 2 h / 80 °C 3: 88 percent / K2CO3 / dimethylformamide / 15 h / 80 °C View Scheme

1: K2CO3; acetone 2: POCl3 View Scheme

sulfuric acid T=20°C; 24 h;

1.1: pyridinium p-toluenesulfonate / toluene / Reflux 1.2: 1.83 h 2.1: potassium dihydrogenphosphate; Fremy’s salt / methanol; water / 1 h / 0 °C 3.1: platinum(IV) oxide; hydrogen / tetrahydrofuran / 2 h / 24 °C 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C 4.2: 20 h / 0 - 24 °C 5.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C 5.2: 1 h / 0 °C 6.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 2 h / 24 °C / Reflux 7.1: toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.4 h / 24 - 50 °C 8.1: platinum(IV) oxide; hydrogen / tetrahydrofuran / 1 h / 24 °C 9.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 9.2: 17 h / -78 - 0 °C / Inert atmosphere 10.1: AlCl3, aluminium chloride; ethane-1,2-dithiol / nitromethane / 0.5 h / -20 °C View Scheme

hydrogenchloride; diethyl ether; zinc(II) chloride beim Erwaermen des Reaktionsprodukts mit H2O;

1: 1.) ZnCl2, HCl(g), 2.) water / 1.) ether, benzene, 0 deg C, 1 d, 2.) ether, benzene, reflux, 1 h 2: 63 percent / BF3*Et2O, PCl5 / 70 °C View Scheme

2: H2SO4 View Scheme

1: H2SO4; acetic acid 2: <1,4>benzoquinone View Scheme

Acidic conditions;