1: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme

1: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature View Scheme

1: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C View Scheme

hydrogenchloride; sodium hydroxide in ethanol 19 h; Heating;