1: 47 percent / Zn, HgCl2, H2O, conc. HCl / toluene / 1 h / Heating 2: 1) n-butyllithium / 1) ether, -50 deg C, 6 h; 2) ether, -50 deg C, 12 h 3: Na / methanol / 6 h / 0 °C 4: 38 percent / N2 / xylene / 5 h / Heating 5: 98 percent / 1) KOH, H2O; 2) 5 N HCl / 1) reflux, 1.5 h, MeOH; 2) 0 deg C, MeOH 6: 60 percent / CuO, Cr2O3 / quinoline / 4 h / 190 - 195 °C View Scheme

1: 82 percent / 3 percent p-toluenesulfonic acid / toluene / 7 h / Heating 2: 1) n-BuLi / 1) ether, -70 deg C, 6 h; 2) ether, 12 h, -70 deg C 3: Na / methanol / 168 h / 0 °C 4: xylene / 3 h / Heating 5: conc. HCl, H2O / ethanol / 18 h 6: 93 percent / KOH, H2O View Scheme

1: 82 percent / 3 percent p-toluenesulfonic acid / toluene / 7 h / Heating 2: 1) n-BuLi / 1) ether, -70 deg C, 6 h; 2) ether, 12 h, -70 deg C 3: Na / methanol / 168 h / 0 °C 4: xylene / 3 h / Heating 5: conc. HCl, H2O / ethanol / 18 h 6: 93 percent / KOH, H2O 7: 54 percent / CuO, Cr2O3 / quinoline / 13 h View Scheme