potassium hydroxide; tetrabutylammomium bromide; water 2.) C6H6, room temperature, 24 h; Yield given. Multistep reaction;

3-chloro-benzenecarboperoxoic acid in dichloromethane T=-78°C; 0.333333 h;

1: 99 percent / MCPBA / CH2Cl2 / 0.33 h / -78 °C 2: 78 percent / toluene / 20 h / Heating 3: 1.) O3, 2.) Me2S / 1.) AcOEt, -78 deg C, 15 min, 2.) -78 deg C, 20 min View Scheme

1: 99 percent / MCPBA / CH2Cl2 / 0.33 h / -78 °C 2: 78 percent / toluene / 20 h / Heating 3: 1.) O3, 2.) Me2S / 1.) AcOEt, -78 deg C, 15 min, 2.) -78 deg C, 20 min 4: 61 percent / H2NOH*HCl, pyridine / methanol / 12 h / Ambient temperature View Scheme

1: 99 percent / MCPBA / CH2Cl2 / 0.33 h / -78 °C 2: 78 percent / toluene / 20 h / Heating 3: 1.) O3, 2.) Me2S / 1.) AcOEt, -78 deg C, 15 min, 2.) -78 deg C, 20 min 4: 61 percent / H2NOH*HCl, pyridine / methanol / 12 h / Ambient temperature 5: 75 percent / H2 / 5percent rhodium-alumina / methanol / 4180 Torr / Ambient temperature View Scheme

1: 99 percent / MCPBA / CH2Cl2 / 0.33 h / -78 °C 2: 78 percent / toluene / 20 h / Heating View Scheme