1: 90 percent / Li/ethylenediamine / 0.25 h / Heating 2: pyridine / 18 h / Ambient temperature 3: 1.) O3, 2.) Jones reagent / 1.) CH2Cl2, -10 deg C, 2.) acetone, 0 deg C 4: 73 percent 5: 72 percent / H2SO4 / ethanol / 24 h / Heating View Scheme

1: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane / 5 h / 0 - 20 °C 2: HIO4*2H2O / tetrahydrofuran / 5 h / 0 - 20 °C 3: potassium hydroxide; oxygen; Food Red No. 105 / methanol / 6 h / 0 °C / |Irradiation 4: Jone's reagent / acetone / 0.25 h / 0 °C View Scheme

1: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane / 5 h / 0 - 20 °C 2: HIO4*2H2O / tetrahydrofuran / 5 h / 0 - 20 °C 3: potassium hydroxide; oxygen; Food Red No. 105 / methanol / 6 h / 0 °C / |Irradiation View Scheme