1: KOH / ethanol / 1 h / Heating 2: 84 percent / HF (g) View Scheme

potassium hydroxide in ethanol 1 h; Heating; Yield given;

1: KOH / ethanol / 1 h / Heating 2: 84 percent / HF (g) 3: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C 4: 93 percent / glacial acetic acid, conc. HCl / 0.25 h 5: 60 percent / 10percent palladium on charcoal / 300 - 305 °C View Scheme

lithium aluminium tetrahydride in tetrahydrofuran T=20°C; 4 h;

1: KOH / ethanol / 1 h / Heating 2: 84 percent / HF (g) 3: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C View Scheme

1: KOH / ethanol / 1 h / Heating 2: 84 percent / HF (g) 3: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C 4: 93 percent / glacial acetic acid, conc. HCl / 0.25 h View Scheme

sulfuric acid T=50°C; 0.666667 h;

hydrogenchloride

sodium tetrahydroborate; tributyltin chloride in ethanol 1.) room temp., 30 min, 2.) reflux, 45 min; Yield given;

1: conc. H2SO4 / benzene / 3 h / Heating 2: 1.) diisobutylaluminum hydride, 2.) conc. HCl / 1.) toluene, hexane, -78 deg C, 1.5 h, 2.) THF, -78 deg C, 5 min 3: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 4: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 5: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min View Scheme