1: 91 percent / benzene / 12 h / Heating 2: 99 percent / NaIO4 / methanol; H2O / 3 h 3: 81 percent / p-toluenesulfonic acid / toluene / 1 h / Heating 4: K2CO3 / methanol / 3 h / 20 °C 5: 1.9 g / Et3N / CH2Cl2 / 12 h 6: 97 percent / Pd(PPh3)2Cl2; Et3N; formic acid / dimethylformamide / 1 h / 110 °C 7: trifluoroacetic acid / 1 h / 100 °C 8: 0.7 g / pyridine / 2 h / 0 °C 9: 75 percent / Pd(PPh3)2Cl2; Et3N; formic acid / dimethylformamide / 1 h / 110 °C 10: 68 percent / potassium permanganate / acetone / 3 h / 20 °C View Scheme

1: 91 percent / benzene / 12 h / Heating 2: 99 percent / NaIO4 / methanol; H2O / 3 h 3: 81 percent / p-toluenesulfonic acid / toluene / 1 h / Heating 4: K2CO3 / methanol / 3 h / 20 °C 5: 1.9 g / Et3N / CH2Cl2 / 12 h 6: 97 percent / Pd(PPh3)2Cl2; Et3N; formic acid / dimethylformamide / 1 h / 110 °C 7: trifluoroacetic acid / 1 h / 100 °C 8: 0.7 g / pyridine / 2 h / 0 °C 9: 75 percent / Pd(PPh3)2Cl2; Et3N; formic acid / dimethylformamide / 1 h / 110 °C View Scheme