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Derivatization of keto fatty acids: V. Synthesis and characterization of 1,3‐dioxolanes
Author(s) -
Ahmad Suhail,
Ahmad F.,
Osman S. M.
Publication year - 1984
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02636366
Subject(s) - dioxolane , chemistry , derivatization , ethylene , reagent , yield (engineering) , organic chemistry , medicinal chemistry , acetal , high performance liquid chromatography , catalysis , materials science , metallurgy
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.