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Synthesis of fatty 2-oxazolines from fatty methyl 2,3-epoxy ester

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Abstract

Reaction of methyltrans-2,3-epoxyhexadecanoate (I) with benzonitrile in presence of boron trifluoride-etherate (BF3-etherate) as catalyst has yieldedcis-2-phenyl-4-tridecyl-5-carbomethoxy-2-oxazoline (II), methyl 2-hydroxy-3-benzamidohexadecanoate (IV) and methyl 2,3-dihydroxyhexadecanoate (III). On the other hand, reactions of I with acetonitrile and acrylonitrile have resulted in the formation of their corresponding hydroxyamides, methyl 2-hydroxy-3-acetamidohexadecanoate (VI) and methyl 2-hydroxy-3-acryloamido hexadecanoate (VII), respectively, along with the product (III) only. Pyrolysis of hydroxyamides (IV), (VI) and (VII) afforded their corresponding 2-oxazolines,cis-2-phenyl-4-tridecyl-5-carboxy-2-oxazoline (V),cis-2-methyl-4-tridecyl-5-carboxy-2-oxazoline (VIII) andcis-2-vinyl-4-tridecyl-5-carboxy-2-oxazoline (IX), respectively, in good yields. The products have been characterized with the help of spectral and microanalyses.

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Correspondence to M. Ahmad.

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Ansari, M.H., Ahmad, M. Synthesis of fatty 2-oxazolines from fatty methyl 2,3-epoxy ester. J Am Oil Chem Soc 63, 908–914 (1986). https://doi.org/10.1007/BF02540926

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Keywords

  • Benzonitrile
  • Geosmin
  • Usual Signal
  • Oxazoline Ring
  • Hydroxyamides