hydrogenchloride; toluene-4-sulfonic acid in methanol; water Ambient temperature1.) 0.5 h, room temp.; 2.) reflux, 3 h;

1: 1.) NaH / 1.) DMF, 30 deg C, 2-3 h; 2.) hexane, room temp., 2 h 2: 1.) n-BuLi, TMEDA / 1.) hexane, 0 - 4 deg C, 1 h; 2.) 1 h 3: 38 percent / HCl, p-toluenesulfonic acid / methanol; H2O / Ambient temperature; 1.) 0.5 h, room temp.; 2.) reflux, 3 h View Scheme

1: 1.) n-BuLi, TMEDA / 1.) hexane, 0 - 4 deg C, 1 h; 2.) 1 h 2: 38 percent / HCl, p-toluenesulfonic acid / methanol; H2O / Ambient temperature; 1.) 0.5 h, room temp.; 2.) reflux, 3 h View Scheme

sodium 1) xylene, 5h, 2) xylene, 24h, 135 deg C; Yield given. Multistep reaction;