1: 78 percent / Na / methanol / 1) 2.5 h, room temperature; 2) 28 h, heating 2: 86 percent / acetic acid / 4 h / 130 °C 3: 94 percent / NaOH / 0.75 h / 100 °C 4: 69 percent / KMnO4, tetrabutylammoniumbromide / benzene; H2O / 1) 1 h, 10 deg C; 2) 30 min, 40 deg C View Scheme

acetic anhydride T=120°C; 1 h; Yield given;

1: 86 percent / Na / methanol / 1) 2.5 h, room temperature; 2) 28 h, heating 2: 39 percent / acetic acid / 4 h / 130 °C 3: 82 percent / NaOH / 0.75 h / 100 °C 4: 27 percent / KMnO4 / H2O / 1) 1 h, 10 deg C; 2) 30 min, 40 deg C View Scheme

1: 50 percent / PCl3 / CHCl3 / 8 h / Heating 2: 1) H2O2 / 1) CH3COOH, H2O, 1 h 40 deg C, 1 h 50 deg C, 1 h 70 deg C, 1 h 80 deg C, 1 h 90 deg C, 17 h 100 deg C. 2) 20 min 125 deg C, 2 h 136-140 deg C 3: 17 percent / KMnO4 / H2O / 1) 1 h, 10 deg C; 2) 30 min, 40 deg C View Scheme

1: 41 percent / 1 h / 120 - 130 °C 2: 68 percent / 10 percent HCl / 1.5 h / 80 °C 3: 86 percent / KMnO4, tetrabutylammoniumbromide / benzene; H2O / 1) 30 min, 5-10 deg C; 2) 30 min, 50 deg C 4: 19 percent / H2S, 25 percent NH3 / 2 h / Heating View Scheme

1: 78 percent / Na / methanol / 1) 2.5 h, room temperature; 2) 28 h, heating 2: 86 percent / acetic acid / 4 h / 130 °C 3: 94 percent / NaOH / 0.75 h / 100 °C View Scheme