1: 1.) diisobutylaluminum hydride, 2.) conc. HCl / 1.) toluene, hexane, -78 deg C, 1.5 h, 2.) THF, -78 deg C, 5 min 2: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 3: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 4: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 5: KOH / ethanol / 1 h / Heating 6: 84 percent / HF (g) View Scheme

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

1: 1.) diisobutylaluminum hydride, 2.) conc. HCl / 1.) toluene, hexane, -78 deg C, 1.5 h, 2.) THF, -78 deg C, 5 min 2: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 3: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 4: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 5: KOH / ethanol / 1 h / Heating 6: 84 percent / HF (g) 7: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C 8: 93 percent / glacial acetic acid, conc. HCl / 0.25 h 9: 60 percent / 10percent palladium on charcoal / 300 - 305 °C View Scheme

1: 1.) diisobutylaluminum hydride, 2.) conc. HCl / 1.) toluene, hexane, -78 deg C, 1.5 h, 2.) THF, -78 deg C, 5 min 2: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 3: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 4: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 5: KOH / ethanol / 1 h / Heating 6: 84 percent / HF (g) 7: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C View Scheme

1: 1.) diisobutylaluminum hydride, 2.) conc. HCl / 1.) toluene, hexane, -78 deg C, 1.5 h, 2.) THF, -78 deg C, 5 min 2: 1.) n-BuLi/N-isopropylcyclohexylamine / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 2 h 3: bromine, triphenyl phosphite / benzene / 1 h / Ambient temperature 4: sodium borohydride, tri-n-butyltin chloride / ethanol / 1.) room temp., 30 min, 2.) reflux, 45 min 5: KOH / ethanol / 1 h / Heating 6: 84 percent / HF (g) 7: 96 percent / sodium borohydride / ethanol / 1.83 h / 55 - 60 °C 8: 93 percent / glacial acetic acid, conc. HCl / 0.25 h View Scheme

sulfuric acid in benzene Yield given;

sodium ethanolate in ethanol 18 h; Heating;

1: 75 percent / NaOEt / ethanol / 18 h / Heating 2: 74 percent / KOH / ethanol / 24 h / Heating View Scheme

1: 75 percent / NaOEt / ethanol / 18 h / Heating 2: 74 percent / KOH / ethanol / 24 h / Heating 3: 71 percent / anhydr. HF View Scheme

1: 75 percent / NaOEt / ethanol / 18 h / Heating 2: 74 percent / KOH / ethanol / 24 h / Heating 3: 71 percent / anhydr. HF 4: 80 percent / Zn(Hg), conc. HCl / H2O; toluene / 24 h / Heating View Scheme