toluene-4-sulfonic acid in chloroform 4 h; Heating;

1: 66 percent / p-toluenesulfonic acid / CHCl3 / 4 h / Heating 2: 99 percent / CHCl3 / 48 h / Ambient temperature; in the dark View Scheme

hydrazine hydrate in ethanol 3 h; Heating;

sodium tetrahydroborate; water; Titanium(IV) oxide in acetonitrile T=20°C; 0.0833333 h; regioselective reaction;

1: 63 percent / hydrazine hydrate / ethanol / 3 h / Heating 2: conc. hydrochloric acid / benzene 3: 57 percent / cerium(IV) ammonium nitrate / H2O; acetonitrile / 0.5 h / Ambient temperature View Scheme