Suhail Ahmad, F. Ahmad, S. Osman
Sep 1, 1984
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0
Influential Citations
3
Citations
Journal
Journal of the American Oil Chemists Society
Abstract
The synthesis of substituted 1,3-dioxolanes from oxo fatty acid esters using 1,2-propanediol is described. This reagent, besides forming dioxolanes, also converts the methyl ester to the 2′-hydroxy propyl ester. Methyl 10-oxoundecanoate gives 2′-hydroxy propyl 10-(2″-methyl ethylene dioxolane) undecanoate (Ia, 75%) as a major product. Methyl 9-oxooctadecanoate reacts similarly and yields 2′-hydroxy propyl 9-(2″-methyl ethylene dioxolane) octadecanoate (IIb, 60%), along with the minor products (IIa, IIc). Methyl 2-oxooctadecanoate, after prolonged refluxing, affords only 2′-hydroxy propyl 2-(2″-methyl ethylene dioxolane) octadecanoate (IIIa) in 70% yield. Structures of each reaction product were established on the basis of elemental analysis, IR, NMR and a study of mass spectrometry.