sulfuric acid in water T=85 - 90°C; 0.5 h; Yield given. Title compound not separated from byproducts;

diethyl ether; benzene

1: benzene; diethyl ether / 0.5 h / 40 °C 2: 52.1 g / 80percent H2SO4 / H2O / 0.5 h / 85 - 90 °C View Scheme

1: benzene; diethyl ether / 0.5 h / 40 °C 2: 52.1 g / 80percent H2SO4 / H2O / 0.5 h / 85 - 90 °C View Scheme

1: 99 percent / 55percent HI, red phosphorus / acetic acid / 5 h / Heating 2: 95 percent / Zn-Cu, 10percent KOH / pyridine; H2O / 16 h / Heating 3: 94 percent / ZnCl2 / acetic acid / 0.83 h / Heating 4: 82 percent / Na2Cr2O7*2H2O / propionic acid / 0.5 h / Heating 5: 53 percent / tetramethylethylenediamine / benzene; diethyl ether / 0.42 h / 30 °C 6: 1.) CH3Li / 1.) THF, 40 deg C, 5 min, 2.) THF, reflux, 7 h 7: 45 percent / sodium / benzene; diethyl ether / 19 h / Ambient temperature View Scheme

phosphorus; hydrogen iodide in acetic acid 5 h; Heating;

1: 99 percent / 55percent HI, red phosphorus / acetic acid / 5 h / Heating 2: 95 percent / Zn-Cu, 10percent KOH / pyridine; H2O / 16 h / Heating 3: 94 percent / ZnCl2 / acetic acid / 0.83 h / Heating 4: 82 percent / Na2Cr2O7*2H2O / propionic acid / 0.5 h / Heating 5: 53 percent / tetramethylethylenediamine / benzene; diethyl ether / 0.42 h / 30 °C View Scheme

1: 99 percent / 55percent HI, red phosphorus / acetic acid / 5 h / Heating 2: 95 percent / Zn-Cu, 10percent KOH / pyridine; H2O / 16 h / Heating 3: 94 percent / ZnCl2 / acetic acid / 0.83 h / Heating 4: 82 percent / Na2Cr2O7*2H2O / propionic acid / 0.5 h / Heating 5: 53 percent / tetramethylethylenediamine / benzene; diethyl ether / 0.42 h / 30 °C 6: 1.) CH3Li / 1.) THF, 40 deg C, 5 min, 2.) THF, reflux, 7 h View Scheme

1: 99 percent / 55percent HI, red phosphorus / acetic acid / 5 h / Heating 2: 95 percent / Zn-Cu, 10percent KOH / pyridine; H2O / 16 h / Heating View Scheme

1: 99 percent / 55percent HI, red phosphorus / acetic acid / 5 h / Heating 2: 95 percent / Zn-Cu, 10percent KOH / pyridine; H2O / 16 h / Heating 3: 94 percent / ZnCl2 / acetic acid / 0.83 h / Heating 4: 82 percent / Na2Cr2O7*2H2O / propionic acid / 0.5 h / Heating View Scheme