1: SOCl2 / 3 h / Heating 2: 85.8 percent / Et3N / diethyl ether / 0.5 h / Ambient temperature 3: 83.8 percent / NaBH4, NaH, 2-propanol / dioxane / 1.) 70 deg C, 2.) reflux, 1 h 4: 95.5 percent / m-chloroperbenzoic acid / CH2Cl2 / Ambient temperature 5: tert-BuOK / dimethylsulfoxide; tetrahydrofuran / 0.17 h / Ambient temperature 6: Al-Hg / tetrahydrofuran; H2O / 0.67 h / Heating View Scheme

1: 85.8 percent / Et3N / diethyl ether / 0.5 h / Ambient temperature 2: 83.8 percent / NaBH4, NaH, 2-propanol / dioxane / 1.) 70 deg C, 2.) reflux, 1 h 3: 95.5 percent / m-chloroperbenzoic acid / CH2Cl2 / Ambient temperature 4: tert-BuOK / dimethylsulfoxide; tetrahydrofuran / 0.17 h / Ambient temperature 5: Al-Hg / tetrahydrofuran; H2O / 0.67 h / Heating View Scheme

1: 83.8 percent / NaBH4, NaH, 2-propanol / dioxane / 1.) 70 deg C, 2.) reflux, 1 h 2: 95.5 percent / m-chloroperbenzoic acid / CH2Cl2 / Ambient temperature 3: tert-BuOK / dimethylsulfoxide; tetrahydrofuran / 0.17 h / Ambient temperature 4: Al-Hg / tetrahydrofuran; H2O / 0.67 h / Heating View Scheme

1: 95.5 percent / m-chloroperbenzoic acid / CH2Cl2 / Ambient temperature 2: tert-BuOK / dimethylsulfoxide; tetrahydrofuran / 0.17 h / Ambient temperature 3: Al-Hg / tetrahydrofuran; H2O / 0.67 h / Heating View Scheme

1: tert-BuOK / dimethylsulfoxide; tetrahydrofuran / 0.17 h / Ambient temperature 2: Al-Hg / tetrahydrofuran; H2O / 0.67 h / Heating View Scheme

dinitrogen monoxide T=250 - 275°C; P=37503.8 - 63006.3 Torr; 10 - 20 h; Product distribution / selectivity;

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 6.1: iodine; potassium hydroxide / -5 - 0 °C 7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 8.1: methanol; water; sodium hydroxide / 5 h / Reflux 8.2: 1 h / Reflux 9.1: iodine; potassium hydroxide / -5 - 0 °C 10.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 11.1: methanol; water; sodium hydroxide / 5 h / Reflux 11.2: 1 h / Reflux 12.1: iodine; potassium hydroxide / -5 - 0 °C 13.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 14.1: methanol; water; sodium hydroxide / 5 h / Reflux 14.2: 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

1.1: 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 6.1: iodine; potassium hydroxide / -5 - 0 °C 7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 8.1: methanol; water; sodium hydroxide / 5 h / Reflux 8.2: 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 6.1: iodine; potassium hydroxide / -5 - 0 °C 7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 8.1: methanol; water; sodium hydroxide / 5 h / Reflux 8.2: 1 h / Reflux 9.1: iodine; potassium hydroxide / -5 - 0 °C 10.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C 11.1: methanol; water; sodium hydroxide / 5 h / Reflux 11.2: 1 h / Reflux View Scheme