1: 1) potassium tert-butoxide / 1) tert-butyl alcohol, reflux, o.5 h, 2) tert-butyl alcohol, reflux, 8 h 2: 82 percent / N,N-dimethylaniline / 2.5 h / 193 °C 3: 84 percent / m-chloroperbenzoic acid / CH2Cl2 / 0 deg C to 22 deg C, 22 h 4: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 5: 82 percent / triethylamine, 4-dimethyl-aminopyridine / CH2Cl2 / 10 h / Ambient temperature 6: 95 percent / benzoyl peroxiden, N-bromosuccinimide / CCl4 / Heating; Irradiation 7: 61 percent / mercuric acetate / 2 h / Heating 8: 86 percent / ammonia, methanol / 10 h / Ambient temperature 9: 78 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 10: 97 percent / p-toluenesulfonic acid / benzene / 4 h / Heating 11: 91 percent / sodium hydroxide, water / tetrahydrofuran / 4 h / 24 °C 12: 70 percent / pyridine, chromium trioxide / CH2Cl2 / 0.5 h / 23 °C 13: 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 14: 51 percent / benzene; methanol / 16 h / Heating 15: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr 16: hydrochloric acid / methanol View Scheme

1: 70 percent / pyridine, chromium trioxide / CH2Cl2 / 0.5 h / 23 °C 2: 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 3: 51 percent / benzene; methanol / 16 h / Heating 4: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr 5: hydrochloric acid / methanol View Scheme

1: 84 percent / m-chloroperbenzoic acid / CH2Cl2 / 0 deg C to 22 deg C, 22 h 2: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 3: 82 percent / triethylamine, 4-dimethyl-aminopyridine / CH2Cl2 / 10 h / Ambient temperature 4: 95 percent / benzoyl peroxiden, N-bromosuccinimide / CCl4 / Heating; Irradiation 5: 61 percent / mercuric acetate / 2 h / Heating 6: 86 percent / ammonia, methanol / 10 h / Ambient temperature 7: 78 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 8: 97 percent / p-toluenesulfonic acid / benzene / 4 h / Heating 9: 91 percent / sodium hydroxide, water / tetrahydrofuran / 4 h / 24 °C 10: 70 percent / pyridine, chromium trioxide / CH2Cl2 / 0.5 h / 23 °C 11: 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 12: 51 percent / benzene; methanol / 16 h / Heating 13: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr 14: hydrochloric acid / methanol View Scheme

1: 82 percent / N,N-dimethylaniline / 2.5 h / 193 °C 2: 84 percent / m-chloroperbenzoic acid / CH2Cl2 / 0 deg C to 22 deg C, 22 h 3: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 4: 82 percent / triethylamine, 4-dimethyl-aminopyridine / CH2Cl2 / 10 h / Ambient temperature 5: 95 percent / benzoyl peroxiden, N-bromosuccinimide / CCl4 / Heating; Irradiation 6: 61 percent / mercuric acetate / 2 h / Heating 7: 86 percent / ammonia, methanol / 10 h / Ambient temperature 8: 78 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 9: 97 percent / p-toluenesulfonic acid / benzene / 4 h / Heating 10: 91 percent / sodium hydroxide, water / tetrahydrofuran / 4 h / 24 °C 11: 70 percent / pyridine, chromium trioxide / CH2Cl2 / 0.5 h / 23 °C 12: 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 13: 51 percent / benzene; methanol / 16 h / Heating 14: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr 15: hydrochloric acid / methanol View Scheme

1: 82 percent / triethylamine, 4-dimethyl-aminopyridine / CH2Cl2 / 10 h / Ambient temperature 2: 95 percent / benzoyl peroxiden, N-bromosuccinimide / CCl4 / Heating; Irradiation 3: 61 percent / mercuric acetate / 2 h / Heating 4: 86 percent / ammonia, methanol / 10 h / Ambient temperature 5: 78 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 6: 97 percent / p-toluenesulfonic acid / benzene / 4 h / Heating 7: 91 percent / sodium hydroxide, water / tetrahydrofuran / 4 h / 24 °C 8: 70 percent / pyridine, chromium trioxide / CH2Cl2 / 0.5 h / 23 °C 9: 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 10: 51 percent / benzene; methanol / 16 h / Heating 11: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr 12: hydrochloric acid / methanol View Scheme

1: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 °C 2: 82 percent / triethylamine, 4-dimethyl-aminopyridine / CH2Cl2 / 10 h / Ambient temperature 3: 95 percent / benzoyl peroxiden, N-bromosuccinimide / CCl4 / Heating; Irradiation 4: 61 percent / mercuric acetate / 2 h / Heating 5: 86 percent / ammonia, methanol / 10 h / Ambient temperature 6: 78 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 7: 97 percent / p-toluenesulfonic acid / benzene / 4 h / Heating 8: 91 percent / sodium hydroxide, water / tetrahydrofuran / 4 h / 24 °C 9: 70 percent / pyridine, chromium trioxide / CH2Cl2 / 0.5 h / 23 °C 10: 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 11: 51 percent / benzene; methanol / 16 h / Heating 12: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr 13: 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 11: hydrochloric acid / methanol View Scheme

1: 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 2: 51 percent / benzene; methanol / 16 h / Heating 3: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr 4: hydrochloric acid / methanol View Scheme

1: 97 percent / p-toluenesulfonic acid / benzene / 4 h / Heating 2: 91 percent / sodium hydroxide, water / tetrahydrofuran / 4 h / 24 °C 3: 70 percent / pyridine, chromium trioxide / CH2Cl2 / 0.5 h / 23 °C 4: 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 5: 51 percent / benzene; methanol / 16 h / Heating 6: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr 7: hydrochloric acid / methanol View Scheme

1: 51 percent / benzene; methanol / 16 h / Heating 2: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr 3: hydrochloric acid / methanol View Scheme