1: H2SO4 / benzene 2: 75 percent / NaOEt / ethanol / 18 h / Heating 3: 81 percent / 85percent KOH / aq. ethanol / 10 h / Heating 4: 83 percent / anhydr. HF 5: 65 percent / 0.11 M KOH, NaBH4 / aq. ethanol / 18 h / Heating 6: 85 percent / conc. HCl / acetic acid / 2 h / Heating 7: 0.6 g / KOH / methanol / 20 h / Heating View Scheme

1: H2SO4 / benzene 2: 75 percent / NaOEt / ethanol / 18 h / Heating 3: 81 percent / 85percent KOH / aq. ethanol / 10 h / Heating 4: 83 percent / anhydr. HF 5: 65 percent / 0.11 M KOH, NaBH4 / aq. ethanol / 18 h / Heating View Scheme

1: With lithium aluminium tetrahydride in tetrahydrofuran T=20°C; 0.5 h; 2: With sulfuric acid in tetrahydrofuran; methanol

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