sulfuric acid T=80°C; 2 h;

1: With sulfuric acid T=74 - 76°C; 1.5 h; 2: With sodium sulfate; acetone in water; toluene T=20°C; 15 h; Product distribution / selectivity;

1: conc. H2SO4 / 60 - 80 °C 2: 5percent aq. NaOH, 30percent H2O2 / 0.5 h / 50 °C View Scheme

1: 55 percent / conc. H2SO4 / 0.75 h / 70 °C 2: 1) 10M NaOH 2) 30percent aq. H2O2 / 1) 70 deg C, 60 min 2) 70 deg C, 60 min 3: 1) 48percent HBr, NaNO2 2) CuBr / 1) water, 1 h, 0 deg C 2) a) 30 min, r.t. b) 90 min, 70 deg C 4: SOCl2 / CH2Cl2 / 1 h / Heating View Scheme

1: With sulfuric acid T=74 - 76°C; 1.5 h; 2: With sodium sulfate; acetone in water; toluene T=20°C; 15 h; Product distribution / selectivity;

1: 55 percent / conc. H2SO4 / 0.75 h / 70 °C 2: 1) 10M NaOH 2) 30percent aq. H2O2 / 1) 70 deg C, 60 min 2) 70 deg C, 60 min 3: 1) 48percent HBr, NaNO2 2) CuBr / 1) water, 1 h, 0 deg C 2) a) 30 min, r.t. b) 90 min, 70 deg C View Scheme

1: 55 percent / conc. H2SO4 / 0.75 h / 70 °C 2: 1) 10M NaOH 2) 30percent aq. H2O2 / 1) 70 deg C, 60 min 2) 70 deg C, 60 min 3: 1) 48percent HBr, NaNO2 2) CuBr / 1) water, 1 h, 0 deg C 2) a) 30 min, r.t. b) 90 min, 70 deg C 4: SOCl2 / CH2Cl2 / 1 h / Heating 5: NH3-gas / CH2Cl2 / 1 h 6: 79 percent / Br2, NaOH / 1) 4 h, 0 deg C 2) 3 h, 60 deg C View Scheme

1: 55 percent / conc. H2SO4 / 0.75 h / 70 °C 2: 1) 10M NaOH 2) 30percent aq. H2O2 / 1) 70 deg C, 60 min 2) 70 deg C, 60 min 3: 1) 48percent HBr, NaNO2 2) CuBr / 1) water, 1 h, 0 deg C 2) a) 30 min, r.t. b) 90 min, 70 deg C 4: SOCl2 / CH2Cl2 / 1 h / Heating 5: NH3-gas / CH2Cl2 / 1 h View Scheme