1: KOH / acetone / 8 h / Heating 2: 75 percent / 1.) H2 (50 psi), 2.) conc. HCl / 5percent Pd on carbon / methanol / 1.5 h 3: 4 N HCl / 4 h / Heating View Scheme

1: KOH / acetone / 8 h / Heating 2: 81 percent / pyridine / CH2Cl2 / 8 h / Heating 3: 96 percent / H2 / 5percent Pd on charcoal / methanol / 4 h / 2585.7 Torr 4: 91 percent / acetic acid, conc. H2SO4 / 6 h / 110 °C View Scheme

sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride in toluene Ambient temperature;

potassium hydroxide in acetone 8 h; Heating; Yield given;