sodium acetate in ethanol; water T=20°C; 3 h; Heating;

1: 84 percent / K2CO3, Bu4NBr / toluene / 20 h / Heating 2: 2N KOH / ethanol / 1 h / Heating 3: 82 percent / CuO / quinoline / 0.5 h / 180 - 200 °C 4: 92 percent / hydrazine hydrate / Raney nickel / methanol / 1 h / Heating 5: 72 percent / 2.) HCl / chlorobenzene / 72 h / Heating 6: 90 percent / NaOAc / ethanol; H2O / 3 h / 20 °C / Heating View Scheme

1: 2N KOH / ethanol / 1 h / Heating 2: 82 percent / CuO / quinoline / 0.5 h / 180 - 200 °C 3: 92 percent / hydrazine hydrate / Raney nickel / methanol / 1 h / Heating 4: 72 percent / 2.) HCl / chlorobenzene / 72 h / Heating 5: 90 percent / NaOAc / ethanol; H2O / 3 h / 20 °C / Heating View Scheme