1: With n-butyllithium in diethyl ether; hexane T=-78 - 25°C; 2: With sodium hydroxide; dihydrogen peroxide 3 h;

Multistep reaction.;

1.1: sodium dithionit / H2O; 2-methoxy-ethanol / 3 h / Heating 1.2: 94 percent / conc. HCl / H2O; 2-methoxy-ethanol / 1 h / Heating View Scheme

1.1: 71 percent / NaNO2; conc. sulfuric acid / 0.06 h / 0 - 20 °C 2.1: sodium dithionit / H2O; 2-methoxy-ethanol / 3 h / Heating 2.2: 94 percent / conc. HCl / H2O; 2-methoxy-ethanol / 1 h / Heating View Scheme

1.1: 50 percent / iodomonochloride / 1,2-dichloro-ethane / 3 h / 70 °C 2.1: 71 percent / NaNO2; conc. sulfuric acid / 0.06 h / 0 - 20 °C 3.1: sodium dithionit / H2O; 2-methoxy-ethanol / 3 h / Heating 3.2: 94 percent / conc. HCl / H2O; 2-methoxy-ethanol / 1 h / Heating View Scheme

1: platinum; acetic acid / Hydrogenation.Behandlung des Reaktionsprodukts mit Schwefelsaeure, Natriumnitrit und Essigsaeure und anschliessend mit einem Gemisch von Natriumjodid, Jod, Harnstoff, Wasser und Chloroform 2: aqueous hydriodic acid; acetic acid View Scheme

1: 92 percent / triethylamine / Pd(PPh3)2Cl2; copper(I) iodide / tetrahydrofuran; dimethylformamide / 4 h / 20 °C 2: 98 percent / Bu4NF / tetrahydrofuran / 0.5 h / 20 °C View Scheme