1.1: sodium hydrogensulfite / water / 2.67 h / 5 °C 1.2: 12 h / 5 - 20 °C 2.1: hydrogenchloride; water / 140 h / 25 °C 3.1: sulfuric acid / Reflux 4.1: sodium hydrogencarbonate; sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / potassium bromide / dichloromethane; water / 2.5 h / -1 - 5 °C View Scheme

1: triethylamine / toluene / 2 h / 0 - 20 °C 2: phosphoric acid / 65 - 75 °C 3: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / |Heating View Scheme

1: 93 percent / p-toluenesulfonic acid / toluene / 2 h / Heating 2: 92 percent / Li, naphthalene / tetrahydrofuran / 2.5 h / -78 °C View Scheme

1: triethylamine / toluene / 2 h / 0 - 20 °C 2: phosphoric acid / 65 - 75 °C View Scheme

n-butyllithium in tetrahydrofuran; hexane T=23°C; 14 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

2.) NaI, acetone; Multistep reaction;

1: 1.) NaI, 2.) p-toluenesulfonic acid / 1.) acetone, reflux, 36 h, 2.) benzene, reflux, 24 h 2: 1.) hexamethyl phosphoric triamide, 2.) HCl / 1.) THF, hexane, -78 degC-RT 4 h, 2.) THF, water, 60 degC-70 degC, 1 h 4: 1.) O2, 2.) p-toluenesulfonic acid / 1.) Sensitox / 1.) CH2Cl2, 30 min, irradiation, 2.) benzene, 24 h, reflux View Scheme