toluene-4-sulfonic acid Yield given;

1: m-chloroperbenzoic acid / CH2Cl2 / 72 h / Ambient temperature 2: p-TsOH / toluene / 1 h / Heating View Scheme

1: 1) LDA / 1) a) THF, hexane, -78 deg C b) to -40 deg C 2) THF, -40 deg C to r.t., 2.5 h 2: 3-chloroperbenzoic acid, KH2PO4, Na2HPO4 / CH2Cl2; H2O / 10 h / 0 °C 3: TsOH / toluene / 1 h / Heating View Scheme

1: 81 percent / AlCl3 / CH2Cl2 3: 1.) hydrogen 2.) conc. H2SO4 / 1.) catalytic View Scheme