toluene-4-sulfonic acid in acetone

toluene-4-sulfonic acid in benzene 1 h; in the dark;

toluene-4-sulfonic acid in benzene 2 h; Heating;

1: 14 percent / diethyl ether / 1.) 0 deg C 1 h: 2.) 3 h room temperature 2: 68 percent / bromine / dioxane / 2 h 3: 88 percent / sodium borohydride / dioxane; H2O / 1.) 2 h at 5 deg C; 2.) 30 min room temperature 4: 78 percent / 10 percent aq potassium carbonate / dioxane / 17 h / Heating; in the dark 5: 95 percent / p-toluenesulfonic acid / benzene / 1 h / in the dark View Scheme

1: 68 percent / bromine / dioxane / 2 h 2: 88 percent / sodium borohydride / dioxane; H2O / 1.) 2 h at 5 deg C; 2.) 30 min room temperature 3: 78 percent / 10 percent aq potassium carbonate / dioxane / 17 h / Heating; in the dark 4: 95 percent / p-toluenesulfonic acid / benzene / 1 h / in the dark View Scheme

1: 78 percent / 10 percent aq potassium carbonate / dioxane / 17 h / Heating; in the dark 2: 95 percent / p-toluenesulfonic acid / benzene / 1 h / in the dark View Scheme

1: 88 percent / sodium borohydride / dioxane; H2O / 1.) 2 h at 5 deg C; 2.) 30 min room temperature 2: 78 percent / 10 percent aq potassium carbonate / dioxane / 17 h / Heating; in the dark 3: 95 percent / p-toluenesulfonic acid / benzene / 1 h / in the dark View Scheme