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Derivatization of keto fatty acids, Part IX. Synthesis and characterization of oxathiolanes
Author(s) -
Ahmad Suhail,
Khan M.,
Nasirullah F. Ahmad,
Osman S. M.
Publication year - 1986
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/bf02679598
Subject(s) - reagent , chemistry , ethylene , derivatization , catalysis , fatty acid , condensation , organic chemistry , high performance liquid chromatography , physics , thermodynamics
Oxathiolanes are prepared from the condensation of the oxo fatty acids with β‐ mercaptoethanol using BF 3 etherate as catalyst. 10‐Oxoundecanoic acid (I) reacts with the reagent promptly and gives 1‐(ethylene oxathiolane) undecanoic acid (V). A similar reaction of 9‐oxooctadecanoic acid (II) yields 9‐(ethylene oxathiolane) octadecanoic acid (VII). Hemimercaptals (VI, VIII) are also isolated as minor products in the above reactions. Methyl 9,10‐dioxooctadecanoate (III) is also found to react readily and affords methyl 9(10)‐ (ethylene oxathiolane)‐ 10(9)oxooctadecanoate (IX) as the sole product. There is no reaction with 2‐oxooctadecanoic acid (IV). The spectral (infrared, nuclear magnetic resonance, mass) properties of oxathiolanes are detailed.