in tetrahydrofuran; acetone

1: 87 percent / LiAlH4 / diethyl ether / 2 h 2: 91 percent / Cl2 / CHCl3 / 5 h / 0 °C View Scheme

1: 87 percent / LiAlH4 / diethyl ether / 2 h 2: 76 percent / Br2 / diethyl ether / 1 h View Scheme

lithium aluminium tetrahydride; copper trifluoromethanesulfonate; sodium hydride 1.) 1,2-dimethoxyethane, reflux, 6 h, 2.) reflux, 3 h, 3.) ether, irradiated, 16 h; Yield given. Multistep reaction. Yields of byproduct given;

lithium aluminium tetrahydride; sodium hydride 1.) 1,2-dimethoxyethane, reflux, 6 h, 2.) reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

1: 87 percent / LiAlH4 / diethyl ether / 2 h 2: 74.2 percent / 3percent aq. KMnO4 / acetone / 0.5 h View Scheme

potassium permanganate in acetone 0.5 h;

potassium hydroxide in ethanol

1.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / Inert atmosphere 1.2: 0.75 h / Inert atmosphere 2.1: sodium hydroxide / ethanol / 4 h / Reflux 3.1: 130 - 140 °C / neat (no solvent) 4.1: thionyl chloride / 1 h / Reflux 5.1: 0.17 h / Reflux 6.1: sodium hydroxide 6.2: 20 h / Reflux 7.1: thionyl chloride 8.1: pyridine; 4-(N,N-dimethlyamino)pyridine / diethyl ether / 0.33 h 9.1: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / benzene / 25 °C / Cooling with liquid nitrogen; Sealed tube; UV-irradiation View Scheme