titanium tetrachloride; zinc in 2-methyl tetrahydrofuran T=15 - 50°C; Product distribution / selectivity;

palladium in ethanol; water; ethyl acetate

1: (Z)-4-(4-chloro-1,2-diphenylbut-1-enyl)phenol With sodium hydride in tetrahydrofuran T=20°C; 1 h; 2: tetrahydro-2-(2-iodoethoxy)-2H-pyran in tetrahydrofuran 9 h; Heating / reflux; 3: With hydrogenchloride; water in ethanol T=20°C; Product distribution / selectivity;

1: With lithium aluminium tetrahydride in tetrahydrofuran 2: With water; ammonium chloride in tetrahydrofuran Product distribution / selectivity;

1: With sodium hydride in tetrahydrofuran T=20°C; 1 h; 2: With 1[(2-iodoethoxy)methyl]benzene in tetrahydrofuran 9 h; Heating / reflux; 3: With acetyl chloride; zinc Product distribution / selectivity;

1: toluene-4-sulfonic acid / toluene / 7 h / |Reflux 2: zinc; titanium tetrachloride / 2-methyl tetrahydrofuran / 2 h / 70 °C 3: lithium aluminium tetrahydride / toluene / 0.5 h / 23 °C / |Inert atmosphere View Scheme

1: polyphosphorip acid / 4 h / |Heating 2: zinc; titanium tetrachloride / 2-methyl tetrahydrofuran / 1.5 h / 70 °C 3: water; potassium hydroxide / tetrahydrofuran; methanol / 20 - 23 °C View Scheme

1: polyphosphorip acid / 4 h / |Heating 2: zinc; titanium tetrachloride / 2-methyl tetrahydrofuran / 1.5 h / 70 °C 3: water; potassium hydroxide / tetrahydrofuran; methanol / 20 - 23 °C View Scheme

1.1: triethylamine / dichloromethane / 0 - 20 °C 2.1: polyphosphoric acid / 3 h / |Heating 3.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / toluene / 0.17 h / 20 °C / |Inert atmosphere 3.2: 12 h / |Inert atmosphere 4.1: tetrahydrofuran / 2 h / 60 °C / |Inert atmosphere 5.1: hydrogenchloride / dichloromethane / 1 h 6.1: sodium hydroxide; water / tetrahydrofuran; methanol / 12 h / 20 °C View Scheme