hydrogenchloride; thionyl chloride; NaHSO4; AlCl3 in ethanol; dichloromethane; water

aluminium trichloride in dichloromethane T=-10°C; 0.25 h;

titanium tetrachloride in dichloromethane T=0 - 20°C; Friedel Crafts reaction; 5 h;

1: thionyl chloride / 1,2-dichloro-ethane / Heating 2: AlCl3 / CH2Cl2 / -5 - 5 °C View Scheme

thionyl chloride

1: 58 percent / NH4Cl / ethanol; H2O / 20 h / 20 °C 2: HCl, HCOOH View Scheme

1: 1.) NaCNBH4, 2.) aq. HCl / 1.) MeOH, RT, 15 h 2: Et3N / CH2Cl2 / 0.17 h / Ambient temperature 3: 41 percent / HN03, H2SO4 / nitromethane / 1 h / -5 °C 4: NH4COOH / Pd/C / methanol / Ambient temperature 5: LiAlH4 / diethyl ether / 15 h / Ambient temperature 6: NH2OH*HCl, Na2SO4 / H2O / 1 h / Heating 7: 1.) 90 percent aq. H2SO4, 2.) LiAlH4 / 1.) a) RT, 0.5 h, b) 80 deg C, 0.5 h, 2.) diethyl ether, RT, 1 h View Scheme