toluene-4-sulfonic acid in methanol T=20°C; Condensation; 18 h;

1: 75 percent / Na2CO3; H2O / methanol / 5 h / 0 °C 2: 90 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / 0 °C 3: 65 percent / p-toluenesulfonic acid / methanol / 18 h / 20 °C View Scheme

1: t-BuOCl / 1 h / 0 °C 2: 14.8 g / CuSO4; H2SO4 / acetic acid / 96 h / 20 °C 3: 75 percent / Na2CO3; H2O / methanol / 5 h / 0 °C 4: 90 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / 0 °C 5: 65 percent / p-toluenesulfonic acid / methanol / 18 h / 20 °C View Scheme

1: 90 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / 0 °C 2: 65 percent / p-toluenesulfonic acid / methanol / 18 h / 20 °C View Scheme

1.1: N-bromosuccinimide; water / acetone / 15 h / 20 °C 1.2: 7.36 g / NaH / dimethylformamide / 15 h / 0 - 20 °C 2.1: 79 percent / NaIO4 / H2O; 2-methyl-propan-2-ol / 15 h / 20 °C 3.1: t-BuOCl / 1 h / 0 °C 4.1: 14.8 g / CuSO4; H2SO4 / acetic acid / 96 h / 20 °C 5.1: 75 percent / Na2CO3; H2O / methanol / 5 h / 0 °C 6.1: 90 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / 0 °C 7.1: 65 percent / p-toluenesulfonic acid / methanol / 18 h / 20 °C View Scheme

dipotassium hydrogenphosphate; potassium dihydrogenphosphate; sodium bromide in dimethyl sulfoxide T=80°C; Oxidation; 20 h;