Abstract
Procedures are described for the preparation of alkyl iodides from fatty alcohols and glyceryl ethers. Alkyl iodides were separated directly by gas-liquid chromatography (GLC) on ethylene glycol succinate columns and do not require calibration factors in their analysis with a thermal conductivity detector. Iodide derivatives have absolute retention times on GLC similar to the corresponding fatty alcohol acetates. Alkyl iodides were converted to alcohol acetates with silver acetate or to hydrocarbons with lithium aluminum hydride and these derivatives were separated by GLC. The elimination of hydriodic acid from secondary iodides during GLC is described. The resulting monoene iodides are readily separated from saturated iodides by GLC. Alkoxy structures have been assigned by comparison of the retention time data of iodide derivatives with standard alcohol derivatives. Unsaturation was confirmed by catalytic hydrogenation. Branched components were identified as the alkanes. Glyceryl ethers were prepared from diacyl glyceryl ethers by hydrogenolysis with lithium aluminum hydride. The glyceryl ether-fatty alcohol mixture was separated quantitatively by thin-layer chromatography (TLC) and sufficient material obtained from one TLC plate for the preparation of alkyl iodide derivatives.
Highlights
The glyceryl ether-fatty alcohol mixture was separated quantitatively by thin-layer chromatography (TLC) and sufficient material obtained from one TLC plate for the preparation of alkyl iodide derivatives
Alcohols and glyceryl ethers were not detected in their alkyl iodide reaction product^,^ and alkyl iodides were not detected in their alcohol acetate reaction products
While alkyl iodides were not separated from hydrocarbons on TLC, their absence from hydrogenolysis products was shown when
Summary
Procedures are described for the preparation of alkyl iodides from fatty alcohols and glyceryl ethers. Alkyl iodides were converted to alcohol acetates with silver acetate or to hydrocarbons with lithium aluminum hydride and these derivatives were separated by GLC. The glyceryl ether-fatty alcohol mixture was separated quantitatively by thin-layer chromatography (TLC) and sufficient material obtained from one TLC plate for the preparation of alkyl iodide derivatives. The glyceryl ethers are converted either to glyceryl ether diacetates (l), dimethoxy glyceryl ethers (2, 3), or alkoxy glycolaldehydes (4), and these derivatives separated by gas-liquid chromatography (GLC) Alcohol acetate, and hydrocarbon derivatives of a glyceryl ether were first prepared by Heilbron and Owens (7), who investigated the structure of batyl alcohol. The reduction mixture, an ethereal solution of glyceryl ethers, sterols, fatty alcohols, arid hydrocarbons, was readily separated into component fractions by thin-layer chromatography (TLC).
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