1: potassium tert-butoxide / 2-methyl-propan-2-ol / 16 h / Heating 2: 50 percent / 48percent aq. HBr / acetic acid / 36 h / Heating 3: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature 4: SOCl2 / toluene / 1.25 h 5: AlCl3 / CS2 / 16 h / Ambient temperature 6: TiCl4 / toluene / 17 h / Ambient temperature 7: sodium borohydride / methanol / 1.5 h / Ambient temperature View Scheme

1: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature 2: SOCl2 / toluene / 1.25 h 3: AlCl3 / CS2 / 16 h / Ambient temperature 4: TiCl4 / toluene / 17 h / Ambient temperature 5: sodium borohydride / methanol / 1.5 h / Ambient temperature View Scheme

1: 50 percent / 48percent aq. HBr / acetic acid / 36 h / Heating 2: 100 percent / H2 / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature 3: SOCl2 / toluene / 1.25 h 4: AlCl3 / CS2 / 16 h / Ambient temperature 5: TiCl4 / toluene / 17 h / Ambient temperature 6: sodium borohydride / methanol / 1.5 h / Ambient temperature View Scheme

1: TiCl4 / toluene / 17 h / Ambient temperature 2: sodium borohydride / methanol / 1.5 h / Ambient temperature View Scheme

sodium tetrahydroborate in methanol 1.5 h; Ambient temperature;

1: SOCl2 / toluene / 1.25 h 2: AlCl3 / CS2 / 16 h / Ambient temperature 3: TiCl4 / toluene / 17 h / Ambient temperature 4: sodium borohydride / methanol / 1.5 h / Ambient temperature View Scheme

1: AlCl3 / CS2 / 16 h / Ambient temperature 2: TiCl4 / toluene / 17 h / Ambient temperature 3: sodium borohydride / methanol / 1.5 h / Ambient temperature View Scheme

1: AlCl3, aluminium chloride 2: ethanol / 0 °C / |Heating; |Industrial scale; |Large scale 3: hydrogen; palladium on activated charcoal View Scheme

1: AlCl3, aluminium chloride 2: ethanol / 0 °C / |Heating; |Industrial scale; |Large scale 3: hydrogen; palladium on activated charcoal View Scheme

hydrogenchloride in diethyl ether; tert-butyl methyl ether