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Metathesis of ethyl oleate, catalyzed by WCl 6 and SnMe 4 , provided diethyl 9‐octadecenedioate (the desired starting material for the synthesis of civetone) in 99% yield. Dieckmann condensation of diethyl 9‐octadecenedioate gave 2‐ethoxycarbonyl‐9‐cycloheptadecenone (63% yield), the hydrolysis‐decarboxylation reaction of which yielded civetone (93%). Identification of all products was by 1 H nuclear magnetic resonance, infrared and mass spectroscopic data. This is the first report of the synthesis of civetone from palm oil‐derived products.
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Choo et al. (1994) studied this question.
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