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Citation: CHEN Xiong, LIU Jinyun, LI Yabai, LIU Jianfu, YANG Huawu. Synthesis of Mintlactone via Cross-Aldol Condensation Between 3-Methylcyclohexanone and Ethyl Pyruvate Using Ferric Chloride Hexahydrate as Catalyst[J]. Chinese Journal of Applied Chemistry, ;2013, 30(9): 1005-1009. doi: 10.3724/SP.J.1095.2013.20523 shu

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

Technology Center, China Tobacco Hunan Industrial Corporation, Changsha 410007, China

Received Date: 14 November 2012
Revised Date: 31 December 2012

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.
- methylcyclohexanone,
- ethyl pyruvate,
- ferric chloride hexahydrate catalyst,
- cross-Aldol condensation,
- mintlactone
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