hydrogen; palladium on activated charcoal in ethanol P=1520 Torr; 4 h; Yield given;

1: SOCl2 2: 32.5 percent / AlCl3 / CH2Cl2 / 1.5 h / -30 °C 3: 1.) p-toluene-sulfonic acid monohydrate; 2.) hydrogen / 2.) PtO2 / 1.) benzene, reflux, 2.5 h; 2.) ethanol, 2.5 atm. 4: hydrogen / 10 percent Pd-on-charcoal / ethanol / 4 h / 1520 Torr View Scheme

1: Na / methanol 2: KOH / methanol 3: SOCl2 4: 32.5 percent / AlCl3 / CH2Cl2 / 1.5 h / -30 °C 5: 1.) p-toluene-sulfonic acid monohydrate; 2.) hydrogen / 2.) PtO2 / 1.) benzene, reflux, 2.5 h; 2.) ethanol, 2.5 atm. 6: hydrogen / 10 percent Pd-on-charcoal / ethanol / 4 h / 1520 Torr View Scheme

1: 32.5 percent / AlCl3 / CH2Cl2 / 1.5 h / -30 °C 2: 1.) p-toluene-sulfonic acid monohydrate; 2.) hydrogen / 2.) PtO2 / 1.) benzene, reflux, 2.5 h; 2.) ethanol, 2.5 atm. 3: hydrogen / 10 percent Pd-on-charcoal / ethanol / 4 h / 1520 Torr View Scheme

1: KOH / methanol 2: SOCl2 3: 32.5 percent / AlCl3 / CH2Cl2 / 1.5 h / -30 °C 4: 1.) p-toluene-sulfonic acid monohydrate; 2.) hydrogen / 2.) PtO2 / 1.) benzene, reflux, 2.5 h; 2.) ethanol, 2.5 atm. 5: hydrogen / 10 percent Pd-on-charcoal / ethanol / 4 h / 1520 Torr View Scheme

1: 1.) p-toluene-sulfonic acid monohydrate; 2.) hydrogen / 2.) PtO2 / 1.) benzene, reflux, 2.5 h; 2.) ethanol, 2.5 atm. 2: hydrogen / 10 percent Pd-on-charcoal / ethanol / 4 h / 1520 Torr View Scheme