lithium aluminium tetrahydride in diethyl ether 1.) room temperature, 2 h, 2.) 30 min, reflux;

1: 6.5 percent Chromat. / LiAlH4 / diethyl ether / other reagent, solvent 2: toluene-p-sulphonic acid / benzene / 15 h / Heating 3: 21 percent Chromat. / NaBH4 / ethanol / 2 h / Ambient temperature; other reagent, solvent View Scheme

lithium aluminium tetrahydride in diethyl ether 1.) room temperature, 2 h, 2.) 30 min, reflux;

3-chloro-benzenecarboperoxoic acid 1.) CH2Cl2, 0 deg C, 2.) 160 deg C to 210 deg C, 14 mm Hg; Multistep reaction;