toluene-4-sulfonic acid in benzene Heating;

1: 1.) O3, 2.) KI, glacial acetic acid / 1.) methanol, -70 deg C, 2.) methanol, room temperature, 1 h 2: 80 percent / p-toluenesulfonic acid / benzene / Heating View Scheme

1.1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 48 h / Reflux; Inert atmosphere 2.1: hydrogenchloride / tetrahydrofuran; water / Reflux; Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere 3.2: 2 h / Inert atmosphere 4.1: sodium / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 4.2: 0 - 20 °C / Inert atmosphere View Scheme

water; lithium; naphthalene 1.) THF, -78 deg C, 3 h, 2.) -78 deg C to 20 deg C, overnight; Yield given. Multistep reaction;