引用本文:
陈雄, 刘金云, 李亚白, 刘建福, 杨华武. 六水合三氯化铁催化3-甲基环己酮与丙酮酸乙酯交叉羟醛缩合制备薄荷内酯[J]. 应用化学,
2013, 30(9): 1005-1009.
doi:
10.3724/SP.J.1095.2013.20523
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
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
六水合三氯化铁催化3-甲基环己酮与丙酮酸乙酯交叉羟醛缩合制备薄荷内酯
摘要:
用FeCl3·6H2O催化3-甲基环己酮与丙酮酸乙酯交叉羟醛缩合,制得2-(2-氧代-4-甲基环己叉基)丙酸乙酯和7a-羟基薄荷内酯,皂化后用硼氢化钠还原、酸化制得(±)-薄荷内酯,产率为51%。考察了3-甲基环己酮的烯醇式异构化的位置选择性和粗产物中(±)-薄荷内酯与(±)-异薄荷内酯异构体的比例。
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关键词:
- 甲基环己酮
- / 丙酮酸乙酯
- / 六水合三氯化铁催化剂
- / 交叉羟醛缩合
- / 薄荷内酯
English
Synthesis of Mintlactone via Cross-Aldol Condensation Between 3-Methylcyclohexanone and Ethyl Pyruvate Using Ferric Chloride Hexahydrate as Catalyst
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.
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