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A convenient preparaton of γ ‐lactones and dialkyltetrahydrofurans from the reaction of fatty acids with epoxides using lithium naphthalenide
Author(s) -
Fujita T.,
Watanabe S.,
Tohtani M.,
Suga K.
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/bf02541642
Subject(s) - tetrahydrofuran , chemistry , lithium (medication) , diethylamine , organic chemistry , potassium , intramolecular force , benzene , medicinal chemistry , solvent , medicine , endocrinology
Fatty acids reacted with epoxides using lithium naphthalenide in the presence of diethylamine to give corresponding 4‐hydroxy acids. These 4‐hydroxy acids easily tended to cyclize into their corresponding γ ‐lactones by refluxing in benzene. Reduction of these γ ‐lactones with lithium aluminum hydride followed by intramolecular dehydration with potassium bisulfate afforded corresponding dialkyl tetrahydrofuran derivatives in high yields. For example, 4‐methyl‐2‐(8‐nonenyl) γ ‐butyrolactone (III) was obtained from 10‐undecylenic acid and propylene oxide. 2‐Methyl‐4‐(8‐nonenyl) tetrahydrofuran (IV) was produced from (III). 2‐Methyl‐4‐(8‐nonenyl) and 2‐ethyl‐4‐(8‐nonenyl) tetrahydrofurans are woody smelling and may be used as perfumery materials.