sodium hydroxide in methanol T=15°C; 3 h;

bis(benzonitrile)palladium(II) dichloride in tetrahydrofuran T=25°C; 1 h;

1: 2) aqueous sulphuric acid / 1) toluene-p-sulphonic acid / 1) a) temperature raised to 95 deg C, 4 h, b) 95 deg C, 4 h, 2) dioxane, 50 deg C, 2 h 2: 51 percent / oxygen / palladium chloride, copper(II) chloride / dimethylformamide; H2O / 70 °C / 1) 150 min, 2) 1 h 3: 87 percent / sodium hydroxide / methanol / 3 h / 15 °C View Scheme

1: 51 percent / oxygen / palladium chloride, copper(II) chloride / dimethylformamide; H2O / 70 °C / 1) 150 min, 2) 1 h 2: 87 percent / sodium hydroxide / methanol / 3 h / 15 °C View Scheme

1: 64 percent / 20percent aqueous oxalic acid / hot 2: 51 percent / oxygen / palladium chloride, copper(II) chloride / dimethylformamide; H2O / 70 °C / 1) 150 min, 2) 1 h 3: 87 percent / sodium hydroxide / methanol / 3 h / 15 °C View Scheme

1: (i) CH2Cl2, SnCl4, (ii) H2O 2: KOH, aq. EtOH View Scheme

2: 67 percent / PdCl2(PhCN)2 / tetrahydrofuran / 1 h / 25 °C View Scheme