hydrogenchloride; toluene-4-sulfonic acid in xylene 7.5 h; Heating;

1: 94 percent / aq. sodium phosphate monobasic dihydrate, 30percent aq. hydrogen peroxide, aq. sodium chlorite / acetonitrile / 4 h / 10 °C 2: 92 percent / K2CO3 / dimethylformamide / 0.17 h / Ambient temperature 3: 93 percent / 1,3-dimethoxybenzene, POCl3 / CHCl3 / 24 h / 60 °C View Scheme

1: 49 percent / 1.) p-toluenesulfonic acid, 2.) aq. 10percent HCl / xylene / 7.5 h / Heating 2: 76 percent / NaBH4 / methanol / 0.5 h / Ambient temperature View Scheme