1: 13.2 g / MeONa / benzene / 15 h / 60 - 62 °C 2: 9.2 g / KOH / H2O / 4 h / Heating 3: 5.2 g / CuO / quinoline / Heating 4: 4.2 g / Ph3P; Br2 / acetonitrile / 8 h / 80 °C 5: 49 percent / benzene / 8 h / 80 °C View Scheme

1: 84 percent / acetic acid / 13 h / 130 °C 2: 5.2 g / KOH / H2O / 6 h / Heating 3: 10.5 g / thionyl chloride / benzene / 6 h / Heating 4: 4 g / aq.NH3 / dioxane; H2O / cooling View Scheme