potassium permanganate; tetrabutylammomium bromide in water; benzene 1) 30 min, 5-10 deg C; 2) 30 min, 50 deg C;

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

1: H2O2 / acetic acid 2: 24 percent / 65 percent HNO3, conc. H2SO4 / 3 h / 93 - 95 °C 3: 41 percent / 1 h / 120 - 130 °C 4: 68 percent / 10 percent HCl / 1.5 h / 80 °C 5: 86 percent / KMnO4, tetrabutylammoniumbromide / benzene; H2O / 1) 30 min, 5-10 deg C; 2) 30 min, 50 deg C View Scheme

1: 24 percent / 65 percent HNO3, conc. H2SO4 / 3 h / 93 - 95 °C 2: 41 percent / 1 h / 120 - 130 °C 3: 68 percent / 10 percent HCl / 1.5 h / 80 °C 4: 86 percent / KMnO4, tetrabutylammoniumbromide / benzene; H2O / 1) 30 min, 5-10 deg C; 2) 30 min, 50 deg C View Scheme

1: 68 percent / 10 percent HCl / 1.5 h / 80 °C 2: 86 percent / KMnO4, tetrabutylammoniumbromide / benzene; H2O / 1) 30 min, 5-10 deg C; 2) 30 min, 50 deg C View Scheme

ammonium hydroxide; hydrogen sulfide 2 h; Heating;