hydrogen catalytic,;

1: SOCl2 2: (i) Mg, (ii) CdCl2, (iii) /BRN= 1921936/ View Scheme

iodine; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium iodide 1) H2O, 12 h, 2) benzene, 70-80 deg C, 3 h; Yield given. Multistep reaction;

1: oxalyl chloride / benzene / 10 - 20 °C 2: aq. NH3 / tetrahydrofuran / 6 h / 0 °C View Scheme

1: 81.6 percent / LAH / diethyl ether / 0 - 20 °C 2: 98.3 percent / pyridine / 0 - 20 °C 3: 59.5 percent / sodium hydride / tetrahydrofuran / 19 h / 0 - 20 °C 4: 95.7 percent / potassium hydroxide / ethanol; H2O / 3 h / Heating 5: 94 percent / decahydronaphthalene / 185 °C 6: 84 percent / LAH / diethyl ether / 0 - 20 °C 7: pyridine / 0 - 20 °C 8: 81.1 percent / LAH / diethyl ether / 0 - 20 °C View Scheme

1: lithium alanate 2: pyridine; phosphorus (III)-bromide View Scheme

1: oxalyl chloride / benzene / Ambient temperature 2: diethyl ether / 0.17 h / -78 °C View Scheme

1: With lithium aluminium tetrahydride in diethyl ether T=20°C; 24 h; Inert atmosphere; 2: With sulfuric acid; water in diethyl ether Cooling with ice;