hydrogen fluoride

1: H2SO4 / benzene 2: 75 percent / NaOEt / ethanol / 18 h / Heating 3: 74 percent / KOH / ethanol / 24 h / Heating 4: 71 percent / anhydr. HF View Scheme

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

hydrogenchloride; mercury; zinc in water; toluene 24 h; Heating;

1: 80 percent / Zn(Hg), conc. HCl / H2O; toluene / 24 h / Heating 2: 65 percent / DDQ / benzene / 24 h / Heating View Scheme

1: 80 percent / Zn(Hg), conc. HCl / H2O; toluene / 24 h / Heating 2: 65 percent / DDQ / benzene / 24 h / Heating 3: 95 percent / LiAlH4 / diethyl ether / 1.) 35 min, reflux, 2.) room temp., overnight View Scheme

1: 80 percent / Zn(Hg), conc. HCl / H2O; toluene / 24 h / Heating 2: 65 percent / DDQ / benzene / 24 h / Heating 3: 95 percent / LiAlH4 / diethyl ether / 1.) 35 min, reflux, 2.) room temp., overnight 4: 71 percent / SOCl2 / benzene / 15 h / Ambient temperature View Scheme