2,3-dicyano-5,6-dichloro-p-benzoquinone in benzene 2 h; Heating;

potassium carbonate in methanol T=40°C; 2 h;

sodium hydroxide in 1,4-dioxane; methanol T=25°C; 0.333333 h;

1: 53 percent / PPh3; DEAD / tetrahydrofuran / 0 - 20 °C 2: 57 percent / Eu(fod)3 / CHCl3 / 18 h / 85 °C / sealed tube 3: 86 percent / (1,3-dimesitylimidazolidin-2-yl)(PCy3)benzylidene-RuCl2 / benzene / 72 h / 20 °C / sealed tube 4: 91 percent / K2CO3 / methanol / 2 h / 40 °C View Scheme

1: 81 percent / pyridine / 20 °C 2: 53 percent / PPh3; DEAD / tetrahydrofuran / 0 - 20 °C 3: 57 percent / Eu(fod)3 / CHCl3 / 18 h / 85 °C / sealed tube 4: 86 percent / (1,3-dimesitylimidazolidin-2-yl)(PCy3)benzylidene-RuCl2 / benzene / 72 h / 20 °C / sealed tube 5: 91 percent / K2CO3 / methanol / 2 h / 40 °C View Scheme

1: 82 percent / potassium carbonate / dimethylformamide / 1 h / 70 °C 2: potassium hydroxide / ethanol / 1 h / Heating 3: 5.48 g / aq. HCl / ethanol; CHCl3 / 1 h / 40 °C 4: 88 percent / potassium carbonate / dimethylformamide / 0.5 h / 60 - 70 °C 5: [hydroxy(tosyloxy)iodo]benzene / CHCl3 / 24 h / 20 °C 6: 3.82 g / aq. sodium hydroxide; methanol / CHCl3 / 5 h / 25 °C 7: 91 percent / triethylamine; PPh3; CuI / PdCl2 / dimethylformamide / 2 h / 80 °C 8: 88 percent / hydrogen / palladium on carbon / methanol; dioxane 9: 85 percent / potassium carbonate / acetone / 0.42 h / 45 °C 10: 84 percent / potassium carbonate / acetone / 2 h / Heating 11: 57 percent / p-TsOH hydrate; acetic acid / toluene / 1.5 h / Heating 12: 91 percent / BCl3 / CH2Cl2 / 2.5 h / 20 - 25 °C 13: 72 percent / aq. sodium hydroxide / methanol; dioxane / 0.33 h / 25 °C View Scheme

1: potassium hydroxide / ethanol / 1 h / Heating 2: 5.48 g / aq. HCl / ethanol; CHCl3 / 1 h / 40 °C 3: 88 percent / potassium carbonate / dimethylformamide / 0.5 h / 60 - 70 °C 4: [hydroxy(tosyloxy)iodo]benzene / CHCl3 / 24 h / 20 °C 5: 3.82 g / aq. sodium hydroxide; methanol / CHCl3 / 5 h / 25 °C 6: 91 percent / triethylamine; PPh3; CuI / PdCl2 / dimethylformamide / 2 h / 80 °C 7: 88 percent / hydrogen / palladium on carbon / methanol; dioxane 8: 85 percent / potassium carbonate / acetone / 0.42 h / 45 °C 9: 84 percent / potassium carbonate / acetone / 2 h / Heating 10: 57 percent / p-TsOH hydrate; acetic acid / toluene / 1.5 h / Heating 11: 91 percent / BCl3 / CH2Cl2 / 2.5 h / 20 - 25 °C 12: 72 percent / aq. sodium hydroxide / methanol; dioxane / 0.33 h / 25 °C View Scheme

1: 91 percent / triethylamine; PPh3; CuI / PdCl2 / dimethylformamide / 2 h / 80 °C 2: 88 percent / hydrogen / palladium on carbon / methanol; dioxane 3: 85 percent / potassium carbonate / acetone / 0.42 h / 45 °C 4: 84 percent / potassium carbonate / acetone / 2 h / Heating 5: 57 percent / p-TsOH hydrate; acetic acid / toluene / 1.5 h / Heating 6: 91 percent / BCl3 / CH2Cl2 / 2.5 h / 20 - 25 °C 7: 72 percent / aq. sodium hydroxide / methanol; dioxane / 0.33 h / 25 °C View Scheme

1: 3.82 g / aq. sodium hydroxide; methanol / CHCl3 / 5 h / 25 °C 2: 91 percent / triethylamine; PPh3; CuI / PdCl2 / dimethylformamide / 2 h / 80 °C 3: 88 percent / hydrogen / palladium on carbon / methanol; dioxane 4: 85 percent / potassium carbonate / acetone / 0.42 h / 45 °C 5: 84 percent / potassium carbonate / acetone / 2 h / Heating 6: 57 percent / p-TsOH hydrate; acetic acid / toluene / 1.5 h / Heating 7: 91 percent / BCl3 / CH2Cl2 / 2.5 h / 20 - 25 °C 8: 72 percent / aq. sodium hydroxide / methanol; dioxane / 0.33 h / 25 °C View Scheme

1: 88 percent / hydrogen / palladium on carbon / methanol; dioxane 2: 85 percent / potassium carbonate / acetone / 0.42 h / 45 °C 3: 84 percent / potassium carbonate / acetone / 2 h / Heating 4: 57 percent / p-TsOH hydrate; acetic acid / toluene / 1.5 h / Heating 5: 91 percent / BCl3 / CH2Cl2 / 2.5 h / 20 - 25 °C 6: 72 percent / aq. sodium hydroxide / methanol; dioxane / 0.33 h / 25 °C View Scheme