sodium in diethyl ether; benzene 19 h; Ambient temperature;

1: benzene; diethyl ether / 0.5 h / 40 °C 2: 80percent H2SO4 / H2O / 0.5 h / 85 - 90 °C 3: 53 percent / tetramethylethylenediamine / benzene; diethyl ether / 0.42 h / 30 °C 4: 1.) CH3Li / 1.) THF, 40 deg C, 5 min, 2.) THF, reflux, 7 h 5: 45 percent / sodium / benzene; diethyl ether / 19 h / Ambient temperature View Scheme

1: 80percent H2SO4 / H2O / 0.5 h / 85 - 90 °C 2: 53 percent / tetramethylethylenediamine / benzene; diethyl ether / 0.42 h / 30 °C 3: 1.) CH3Li / 1.) THF, 40 deg C, 5 min, 2.) THF, reflux, 7 h 4: 45 percent / sodium / benzene; diethyl ether / 19 h / Ambient temperature View Scheme

1: 1.) CH3Li / 1.) THF, 40 deg C, 5 min, 2.) THF, reflux, 7 h 2: 45 percent / sodium / benzene; diethyl ether / 19 h / Ambient temperature View Scheme

1: 53 percent / tetramethylethylenediamine / benzene; diethyl ether / 0.42 h / 30 °C 2: 1.) CH3Li / 1.) THF, 40 deg C, 5 min, 2.) THF, reflux, 7 h 3: 45 percent / sodium / benzene; diethyl ether / 19 h / Ambient temperature 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

1: 94 percent / ZnCl2 / acetic acid / 0.83 h / Heating 2: 82 percent / Na2Cr2O7*2H2O / propionic acid / 0.5 h / Heating 3: 53 percent / tetramethylethylenediamine / benzene; diethyl ether / 0.42 h / 30 °C 4: 1.) CH3Li / 1.) THF, 40 deg C, 5 min, 2.) THF, reflux, 7 h 5: 45 percent / sodium / benzene; diethyl ether / 19 h / Ambient temperature View Scheme

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

1: 82 percent / Na2Cr2O7*2H2O / propionic acid / 0.5 h / Heating 2: 53 percent / tetramethylethylenediamine / benzene; diethyl ether / 0.42 h / 30 °C 3: 1.) CH3Li / 1.) THF, 40 deg C, 5 min, 2.) THF, reflux, 7 h 4: 45 percent / sodium / benzene; diethyl ether / 19 h / Ambient temperature View Scheme

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