1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 2.1: methanol; water; sodium hydroxide / 5 h / Reflux 2.2: 1 h / Reflux View Scheme

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 2.1: methanol; water; sodium hydroxide / 5 h / Reflux 2.2: 1 h / Reflux 3.1: iodine; potassium hydroxide / -5 - 0 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 5.1: methanol; water; sodium hydroxide / 5 h / Reflux 5.2: 1 h / Reflux View Scheme

1: 96 percent / 73percent di-isobutylaluminium hydride / diethyl ether / 1.) -70 deg C, 1 h, 2.) -70 deg C - 0 deg C, 1 h 2: 86 percent / Ph3P, CBr4 / diethyl ether / 6 h / 4 - 5 °C 3: 94 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating 4: 1.) BF3.Et2O, NaBH4, 2.) 3N NaOH, 30percent H2O2 / 1.) THF, 20 deg C, 2.5 h, 2.) THF, overnight 5: 82 percent / CrO3, 6 N H2SO4 / acetone / 0.5 h / 0 °C 6: 67 percent / m-chloroperbenzoic acid / CCl4 / 1.) 20 deg C, 5 h, 2.) 50 deg C, 0.5 h View Scheme