Editing Synthesis of Lipids (section)

== Synthesis of Cholesteryl Iodide and Cholesteryl Chloride<br>  ==

<br> 

Cholesteryl Iodide.-To 20.0 g (0.13 mole) of sodium iodide in 200 ml of acetone at 35 oC (constant-temperature bath) were added 5.0 g (0.0110 mole) of cholesteryl chloroformate and then sufficient diethyl ether ( ~ 2 ml) 0 to make the solution homogeneous. Precipitation of sodium chloride was observed and, after<br>70 hr, the solution was evaporated to dryness under reduced pressure. The residue was dissolved using 100 ml of diethyl ether and 100 mi of water. The ether layer was washed with 50 ml of dilute sodium hydrogen sulfite solution and then with 25 ml of water, followed by evaporation to dryness. The residue was recrystallized from acetone to give 2.9 g of a white crystalline solid. A second recrystallization from acetone gave 2.7 g of cholesteryl iodide (49% yield).<br> 

Cholesteryl Chloride.-To 50 ml of acetone were added 5.0 g (0.0110 mole) of cholesteryl chloroformate and 10.0 g (0.17 mole) of sodium chloride and the mixture was refluxed for 250<br>hr. After cooling, the mixture was filtered and the precipitate was washed with 25 ml of diethyl ether. The ether was added to the mother liquor, which was then evaporated to dryness<br>under reduced pressure, and the residue was recrystallized twice from acetone to give 3.0 g of white crystalline cholesteryl chloride (67% yield)<br> 

<br>