1: 1.) AcOH, Ac2O, H2SO4, 2.) SnCl4, 3.) MeONa 2: 55 percent / PhOCO2Ph, NaHCO3 / 4 h / 140 - 150 °C 3: 85 percent / pyridinium bromide, pyridine / 3 h / Heating 4: 90 percent / H2 / Raney Ni / methanol / 2327.2 Torr View Scheme

1: 1.) AcOH, Ac2O, H2SO4, 2.) SnCl4, 3.) MeONa 2: 55 percent / PhOCO2Ph, NaHCO3 / 4 h / 140 - 150 °C View Scheme

hydrazine hydrate in pyridine 16 h; Ambient temperature;

1: 1.) AcOH, Ac2O, H2SO4, 2.) SnCl4, 3.) MeONa 2: 55 percent / PhOCO2Ph, NaHCO3 / 4 h / 140 - 150 °C 3: 85 percent / pyridinium bromide, pyridine / 3 h / Heating View Scheme

sulfuric acid; sodium methylate; acetic anhydride; tin(IV) chloride; acetic acid Yield given. Multistep reaction;