Sodium Iodide → HCID 10407167, compound

Participants

Reaction Steps

A solution of linoleyl alcohol (5.32 g, 200 mmole) and pyridine (40 ml) was cooled to 0° C. and added to p-toluene-sulfonic chloride (4.2 g, 220 mmole) in 10 ml of pyridine. The resulting solution was stirred overnight at 0° C. and poured into 50 ml of ice water. The organic layer was extracted with 100 ml of ether and the organic layer was washed with 1% aqueous hydrochloric acid until acidic and then washed three times with water. The organic solution was dried over magnesium sulfate, filtered and the solvent evaporated to give 6 g of oily material having an Rf of 0.3 on thin layer chromatography (20Δ ethyl acetate/Skelly B linoleyl alcohol Rf =0.1). To the crude tosylate (6 g, 140 mmole) was added acetone (150 ml) and sodium iodide (300 mmole, 4.5 g), and the mixture was heated gently on a steam bath for 3 hours. The solvent was removed in vacuo and 200 ml of ether added thereto. The organic layer was washed twice with an aqueous solution of sodium bisulfite, twice with water and dried over magnesium sulfate, filtered and solvent removed. The crude iodide was purified by column chromatography over silica gel and eluted with Skelly B to yield 5.2 g of linoleyl iodide Rf ethyl acetate--Skelly B (10:90 v/v)=0.7 of formula II of Chart A.

Provenance & Evidence