1: PCl5 / benzene / 3 h / Ambient temperature 2: 62 percent / AlCl3 / 2 h / Ambient temperature View Scheme

1: H2SO4 / Heating 2: benzene / 0 °C 3: 85 percent / ZnI2 / 1,2-dichloro-ethane / Ambient temperature 4: 1.) i-Pr2NLi, HCO2Et, 2.) p-MeC6H4SO2N3, Et3N / 1.) THF, -78 deg C, 2.) CH2Cl2, r.t. 5: Rh2(OAc)4 / benzene / Heating 6: m-ClC6H4CO3H, aq. NaHCO3 / CH2Cl2 / Ambient temperature 7: NiCl2*6H2O, NaBH4 / methanol / Ambient temperature 8: i-Pr2NLi, HMPA / tetrahydrofuran / Ambient temperature 9: LiAlH4 / diethyl ether / Ambient temperature 10: pyridinium chlorochromate / CH2Cl2 / Ambient temperature 11: H2NNH2*H2O, Na / ethane-1,2-diol; bis-(2-hydroxy-ethyl) ether / 185 °C View Scheme

sulfuric acid 5 h; Heating;

hydrazine hydrate; diethylene glycol T=135°C; anschliessend Erhitzen mit KOH auf 220grad;

1: PCl5 / benzene / 3 h / Ambient temperature 2: 41 percent / AlCl3 / 2 h / Ambient temperature 3: 56 percent / hydrazine hydrate, concd HCl / ethanol / 4 h / Heating 4: 39 percent / sulfuryl chloride / CH2Cl2 / 1 h / Ambient temperature 5: 47 percent / Na, diethyl malonate / benzene; ethanol / 2 h / Heating 6: 16.5 percent / toluene / 4 h / Heating View Scheme