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

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