1: PCl5, POCl3 / Heating 2: ethanol / 5 h / Heating 3: H2 / 5percent Pd/C / aq. ethanol / 2327.2 Torr 4: HCl / ethanol / 1.) 25 deg C, 5 h, 2.) reflux, 1.5 h 5: MnO2, 5 M NaOH / H2O / 0.83 h / pH 6 View Scheme

1: ethanol / 5 h / Heating 2: H2 / 5percent Pd/C / aq. ethanol / 2327.2 Torr 3: HCl / ethanol / 1.) 25 deg C, 5 h, 2.) reflux, 1.5 h 4: MnO2, 5 M NaOH / H2O / 0.83 h / pH 6 View Scheme

1: 1.) Ac2O, 2.) NaOAc / 1.) reflux, 1 h, 2.) a) 100 deg C, b) 25 deg C, overnight 2: PCl5, POCl3 / Heating 3: ethanol / 5 h / Heating 4: H2 / 5percent Pd/C / aq. ethanol / 2327.2 Torr 5: HCl / ethanol / 1.) 25 deg C, 5 h, 2.) reflux, 1.5 h 6: MnO2, 5 M NaOH / H2O / 0.83 h / pH 6 View Scheme

manganese(IV) oxide; sodium hydroxide in water 0.833333 h; pH 6; Yield given;