pyridine 24 h; Heating;

3-chloro-benzenecarboperoxoic acid in dichloromethane T=20°C; 24 h;

1: 86 percent / Raney Nickel; H2 / methanol / 5 h / 3361.46 Torr 2: 95 percent / potassium hydroxide; tetrabutylammonium bromide / tetrahydrofuran / 6 h / 20 °C 3: 75 percent / meta-chloroperbenzoic acid / CH2Cl2 / 24 h / 20 °C View Scheme

1: 98 percent / KO-tBu / dimethylsulfoxide / 2 h / 40 °C 2: 95 percent / diethyl zinc / hexane / 6 h / 0 °C 3: 86 percent / Raney Nickel; H2 / methanol / 5 h / 3361.46 Torr 4: 95 percent / potassium hydroxide; tetrabutylammonium bromide / tetrahydrofuran / 6 h / 20 °C 5: 75 percent / meta-chloroperbenzoic acid / CH2Cl2 / 24 h / 20 °C View Scheme

1: 86 percent / LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 2.) DMF, 60 deg, 18 h 3: 84 percent / H2 / 5percent Pd/C / tetrahydrofuran / 50 - 60 °C / 2585.7 Torr 4: NaOH / H2O / 12 h / Ambient temperature View Scheme

1: 95 percent / diethyl zinc / hexane / 6 h / 0 °C 2: 86 percent / Raney Nickel; H2 / methanol / 5 h / 3361.46 Torr 3: 95 percent / potassium hydroxide; tetrabutylammonium bromide / tetrahydrofuran / 6 h / 20 °C 4: 75 percent / meta-chloroperbenzoic acid / CH2Cl2 / 24 h / 20 °C View Scheme

1: 90 percent / KOH; tetrabutylammonium bromide / tetrahydrofuran / 5 h / 20 °C 2: 98 percent / KO-tBu / dimethylsulfoxide / 2 h / 40 °C 3: 95 percent / diethyl zinc / hexane / 6 h / 0 °C 4: 86 percent / Raney Nickel; H2 / methanol / 5 h / 3361.46 Torr 5: 95 percent / potassium hydroxide; tetrabutylammonium bromide / tetrahydrofuran / 6 h / 20 °C 6: 75 percent / meta-chloroperbenzoic acid / CH2Cl2 / 24 h / 20 °C View Scheme

1: 95 percent / potassium hydroxide; tetrabutylammonium bromide / tetrahydrofuran / 6 h / 20 °C 2: 75 percent / meta-chloroperbenzoic acid / CH2Cl2 / 24 h / 20 °C View Scheme

base

24 h; Ambient temperature;