Chinese Journal of Applied Chemistry

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Synthesis of Mintlactone via Cross-Aldol Condensation Between 3-Methylcyclohexanone and Ethyl Pyruvate Using Ferric Chloride Hexahydrate as Catalyst

CHEN Xiong, LIU Jinyun, LI Yabai, LIU Jianfu, YANG Huawu*   

  1. (Technology Center,China Tobacco Hunan Industrial Corporation,Changsha 410007,China)
  • Received:2012-11-14 Revised:2012-12-28 Published:2013-09-10 Online:2013-09-10
  • Contact: Hua-wu YANG

Abstract: A FeCl3·6H2O-catalyzed cross-Aldol condensation of 3-methylcyclohexanone and ethyl pyruvate was developed for the synthesis of mintlactone. The resultant ethyl 2-(4-methyl-2-oxocyclohexylidene) propionate and 7a-hydroxymintlactone were saponified by NaOH, reduced by NaBH4, and acidified to yield (±)-mintlactone in 51% yield. Regioselectivity of the keto-to-enol isomerization of 3-methylcyclohexanone and isomer ratio of (±)-mintlactone/(±)-isomintlactone in crude products were discussed.

Key words: methylcyclohexanone, ethyl pyruvate, ferric chloride hexahydrate catalyst, cross-Aldol condensation, mintlactone

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