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

1: 78 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 2: 97 percent / p-toluenesulfonic acid / benzene / 4 h / Heating 3: 91 percent / sodium hydroxide, water / tetrahydrofuran / 4 h / 24 °C 4: 70 percent / pyridine, chromium trioxide / CH2Cl2 / 0.5 h / 23 °C 5: 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 6: 51 percent / benzene; methanol / 16 h / Heating 7: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr 8: hydrochloric acid / methanol View Scheme

1: 84 percent / hydrogen, triethylamine / 5 percent palladium on carbon / ethanol / 775.7 Torr 2: hydrochloric acid / methanol View Scheme

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

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

hydrogenchloride in methanol