toluene-4-sulfonic acid in benzene 7 h; Heating;

1: hydrogenchloride; sodium iodide / acetonitrile / 80 - 90 °C 2: toluene-4-sulfonic acid / toluene / Reflux View Scheme

1: trichlorophosphate / 70 - 80 °C 2: hydrogenchloride; sodium iodide / acetonitrile / 80 - 90 °C 3: toluene-4-sulfonic acid / toluene / Reflux View Scheme

1.1: n-BuLi / diethyl ether; hexane / -70 °C 1.2: 64 percent / diethyl ether; hexane / 1 h / -70 - 20 °C 2.1: 92 percent / HCl / H2O; diethyl ether / 1 h / 20 °C 3.1: methanol / 1 h / 20 °C 3.2: 80 percent / sodium borohydride; methanol / 1 h / 0 °C 4.1: 74 percent / benzene / 2 h / Heating View Scheme

1.1: n-BuLi / diethyl ether; hexane / -70 °C 1.2: 64 percent / diethyl ether; hexane / 1 h / -70 - 20 °C 2.1: 92 percent / HCl / H2O; diethyl ether / 1 h / 20 °C View Scheme

1.1: n-BuLi / diethyl ether; hexane / -70 °C 1.2: 64 percent / diethyl ether; hexane / 1 h / -70 - 20 °C 2.1: 92 percent / HCl / H2O; diethyl ether / 1 h / 20 °C 3.1: methanol / 1 h / 20 °C 3.2: 80 percent / sodium borohydride; methanol / 1 h / 0 °C 4.1: 74 percent / benzene / 2 h / Heating View Scheme