triethylamine in tetrahydrofuran T=40°C; 48 h;

1: 5 Pd/C; hydrogen / ethyl acetate / 6.5 h / 65 °C / 3750.38 Torr 2: sodium hydrogencarbonate / acetone / 30 °C / |Reflux 3: AlCl3, aluminium chloride; sodium chloride / 3 h / 140 °C 4: sodium hydroxide / dimethyl sulfoxide / 12 h / 50 °C 5: ethanol / 8 h / |Reflux View Scheme

in water 25.5 h;

1: 85 percent KOH / 4 h / 50 - 55 °C 2: 48 percent HBr / acetone; H2O / 3 h 3: 71.2 percent / H2O / 25.5 h View Scheme

1: sodium hydroxide / water / 0.17 h / 90 - 95 °C 2: AlCl3, aluminium chloride / nitrobenzene / 6.5 h / 20 - 140 °C 3: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 10 h / 75 °C 4: water / 12 h / 20 °C 5: palladium 10 on activated carbon; hydrogen / methanol / 20 °C / 1034.32 Torr 6: triethylamine / tetrahydrofuran / 48 h / 40 °C View Scheme

1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 10 h / 75 °C 2: water / 12 h / 20 °C 3: palladium 10 on activated carbon; hydrogen / methanol / 20 °C / 1034.32 Torr 4: triethylamine / tetrahydrofuran / 48 h / 40 °C View Scheme

1: water / 12 h / 20 °C 2: palladium 10 on activated carbon; hydrogen / methanol / 20 °C / 1034.32 Torr 3: triethylamine / tetrahydrofuran / 48 h / 40 °C View Scheme

1: 93.4 percent / AlCl3 / nitrobenzene / 4.5 h / 25 - 30 °C 2: 85 percent KOH / 4 h / 50 - 55 °C 3: 48 percent HBr / acetone; H2O / 3 h 4: 71.2 percent / H2O / 25.5 h View Scheme

1: 91.6 percent / KHCO3 / acetone / 48 h / 20 - 30 °C 2: 93.4 percent / AlCl3 / nitrobenzene / 4.5 h / 25 - 30 °C 3: 85 percent KOH / 4 h / 50 - 55 °C 4: 48 percent HBr / acetone; H2O / 3 h 5: 71.2 percent / H2O / 25.5 h View Scheme

1: 91.6 percent / KHCO3 / acetone / 48 h / 20 - 30 °C 2: 93.4 percent / AlCl3 / nitrobenzene / 4.5 h / 25 - 30 °C 3: 85 percent KOH / 4 h / 50 - 55 °C 4: 48 percent HBr / acetone; H2O / 3 h 5: 71.2 percent / H2O / 25.5 h View Scheme