1: acetone / Jones oxidation 2: H2SO4 / Heating 3: benzene / 0 °C 4: 85 percent / ZnI2 / 1,2-dichloro-ethane / Ambient temperature 5: 1.) i-Pr2NLi, HCO2Et, 2.) p-MeC6H4SO2N3, Et3N / 1.) THF, -78 deg C, 2.) CH2Cl2, r.t. 6: Rh2(OAc)4 / benzene / Heating 7: m-ClC6H4CO3H, aq. NaHCO3 / CH2Cl2 / Ambient temperature 8: NiCl2*6H2O, NaBH4 / methanol / Ambient temperature 9: i-Pr2NLi, HMPA / tetrahydrofuran / Ambient temperature 10: LiAlH4 / diethyl ether / Ambient temperature 11: pyridinium chlorochromate / CH2Cl2 / Ambient temperature 12: H2NNH2*H2O, Na / ethane-1,2-diol; bis-(2-hydroxy-ethyl) ether / 185 °C View Scheme

jones reagent in acetone T=0°C; 0.5 h; Yield given;

1: acetone / Jones oxidation 2: H2SO4 / Heating View Scheme