Journal of the American Oil Chemists' Society p. 911 - 913 (1994)
Update date:2022-08-11
Topics:
Choo, Yuen-May
Ooi, Kay-Eng
Ooi, Ing-Hong
Methathesis of ethyl oleate, catalyzed by WCl6 and SnMe4, provided diethyl 9-octadecenedioate (the desired starting material for the synthesis of civetone) in 99percent yield.Dieckmann condensation of diethyl 9-octadecenedioate gave 2-ethoxycarbonyl-9-cycloheptadecenone (63percent yield), the hydrolysis-decarboxylation reaction of which yielded civetone (93percent).Identiffication of all products was by 1H nuclear magnetic resonance, infrared and mass spectroscopic data.This is the first report of the synthesis of civetone from palm oil-derived products.KEY WORDS: Civet, civetone, diethyl 9-octadecenedioate, 2-ethoxycarbonyl-9-cycloheptadecenone, ethyl oleate, metathesis, palm oil.
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