SYNTHESIS OF ETHYL HEXYL ETHER

• Place 204 g (250 ml, 2mol) of dry hexan-1-ol in a 500-ml round-bottomed flask fitted with a Liebig-type reflux condenser and introduce 5.75 g (0.25 mol) of clean sodium in small pieces and warm under reflux until all the sodium has reacted (c. 2 hours). 

• Introduce 39 g (20 ml, 0.25 mol) of ethyl iodide down the condenser from a dropping funnel and reflux gently for 2 hours; sodium iodide gradually separates. 

• Arrange the apparatus for downward distillation and collect the crude ether at 143-148 °C (27 g). 

• When cold, refit the reflux condenser, add a further 5.75 g (0.25 mol) of clean sodium and warm until all has reacted: alternatively, allow the reaction to proceed overnight, by which time all the sodium will have reacted. 

• Introduce a further 39 g (20 ml, 0.25 mol) of ethyl iodide and reflux for 2 hours; distil off the crude ether and collect the fraction passing over at 143-148 °C. 

• Combine the two distillates. 

• Remove most of the hexan-1-ol still present in the crude ether by heating under reflux for 2 hours with a large excess of sodium and then distil until no more liquid passes over. 

• Distil the resulting liquid from a few grams of sodium using a short fractionating column, and collect the ethyl hexyl ether at 140-143 °C. The yield is 30 g (46%). 

• If the sodium is appreciably attacked, indicating that all the alcohol has not been completely removed, repeat the distillation from a little fresh sodium.