1: 95 percent / benzoyl peroxiden, N-bromosuccinimide / CCl4 / Heating; Irradiation 2: 61 percent / mercuric acetate / 2 h / Heating 3: 86 percent / ammonia, methanol / 10 h / Ambient temperature 4: 78 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 5: 97 percent / p-toluenesulfonic acid / benzene / 4 h / Heating 6: 91 percent / sodium hydroxide, water / tetrahydrofuran / 4 h / 24 °C 7: 70 percent / pyridine, chromium trioxide / CH2Cl2 / 0.5 h / 23 °C 8: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 25 deg C, 1 h 9: 51 percent / benzene; methanol / 16 h / Heating 10: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr 11: hydrochloric acid / methanol View Scheme

1: 95 percent / benzoyl peroxiden, N-bromosuccinimide / CCl4 / Heating; Irradiation 2: 61 percent / mercuric acetate / 2 h / Heating 3: 86 percent / ammonia, methanol / 10 h / Ambient temperature 4: 78 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 5: 97 percent / p-toluenesulfonic acid / benzene / 4 h / Heating 6: 91 percent / sodium hydroxide, water / tetrahydrofuran / 4 h / 24 °C 7: 70 percent / pyridine, chromium trioxide / CH2Cl2 / 0.5 h / 23 °C 8: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 25 deg C, 1 h 9: 51 percent / benzene; methanol / 16 h / Heating 10: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr View Scheme