1: Fe / ethanol; H2O; acetic acid / 2 h / Heating 2: 99 percent / CHCl3 3: 1. N2H4; 2. aq. NH3 / 1. pyridine, ethanol, H2O, 60 to 65 deg C, 2 h; 2. H2O, 20 min 4: 78 percent / P2S5 / pyridine / 0.75 h / Heating 5: 64 percent / butan-1-ol / 7.5 h / Heating View Scheme

1: Fe / ethanol; H2O; acetic acid / 2 h / Heating 2: 99 percent / CHCl3 3: 1. N2H4; 2. aq. NH3 / 1. pyridine, ethanol, H2O, 60 to 65 deg C, 2 h; 2. H2O, 20 min 4: 78 percent / P2S5 / pyridine / 0.75 h / Heating 5: 70 percent / butan-1-ol / Heating View Scheme

potassium hydroxide in methanol; water; benzene 3 h; Ambient temperature;