Home

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
1. [1]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
2. [2]
  Jinghua Wang , Yanxin Yu , Yanbiao Ren , Yesheng Wang . Integration of Science and Education: Investigation of Tributyl Citrate Synthesis under the Promotion of Hydrate Molten Salts for Research and Innovation Training. University Chemistry, 2024, 39(11): 232-240. doi: 10.3866/PKU.DXHX202402057
3. [3]
  Yajin Li , Huimin Liu , Lan Ma , Jiaxiong Liu , Dehua He . Photothermal Synthesis of Glycerol Carbonate via Glycerol Carbonylation with CO₂ over Au/Co₃O₄-ZnO Catalyst. Acta Physico-Chimica Sinica, 2024, 40(9): 2308005-0. doi: 10.3866/PKU.WHXB202308005
4. [4]
  Mengyang LI , Hao XU , Zhonghao NIU , Chunhua GONG , Weihui ZHONG , Jingli XIE . Highly effective catalytic synthesis of β-amino alcohols by using viologen-polyoxometalate hybrid materials. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1294-1300. doi: 10.11862/CJIC.20250080
5. [5]
  Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095
6. [6]
  Yihui Song , Shangshang Qin , Kai Wu , Chengyun Jin , Bin Yu . 生物化学在高水平创新型药学人才培养中的交叉融合应用——以去甲基化酶LSD1抑制剂的活性评价为例. University Chemistry, 2025, 40(6): 341-352. doi: 10.12461/PKU.DXHX202406018
7. [7]
  Zongsheng LI , Yichao WANG , Yujie WANG , Wenhao ZHU , Xiaoyao YIN , Wudan YANG , Songzhi ZHENG , Weihai SUN . Preparation of CsPbBr₃ perovskite solar cells via bottom interface modification with methylammonium chloride. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1805-1816. doi: 10.11862/CJIC.20250066
8. [8]
  Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
9. [9]
  Shuying Zhu , Shuting Wu , Ou Zheng . Improvement and Expansion of the Experiment for Determining the Rate Constant of the Saponification Reaction of Ethyl Acetate. University Chemistry, 2024, 39(4): 107-113. doi: 10.3866/PKU.DXHX202310117
10. [10]
  Ruitong Zhang , Zhiqiang Zeng , Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004
11. [11]
  Jiaojiao Yu , Bo Sun , Na Li , Cong Wen , Wei Li . Improvement of Classical Organic Experiment Based on the “Reverse-Step Optimization Method”: Taking Synthesis of Ethyl Acetate as an Example. University Chemistry, 2025, 40(3): 333-341. doi: 10.12461/PKU.DXHX202405177
12. [12]
  Xichen YAO , Shuxian WANG , Yun WANG , Cheng WANG , Chuang ZHANG . Oxygen reduction performance of self?supported Fe/N/C three-dimensional aerogel catalyst layers. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1387-1396. doi: 10.11862/CJIC.20240384
13. [13]
  Rong Tian , Yadi Yang , Naihao Lu . Comprehensive Experimental Design of Undergraduate Students Based on Interdisciplinarity: Study on the Effect of Quercetin on Chlorination Activity of Myeloperoxidase. University Chemistry, 2024, 39(8): 247-254. doi: 10.3866/PKU.DXHX202312064
14. [14]
  Meiran Li , Yingjie Song , Xin Wan , Yang Li , Yiqi Luo , Yeheng He , Bowen Xia , Hua Zhou , Mingfei Shao . Nickel-Vanadium Layered Double Hydroxides for Efficient and Scalable Electrooxidation of 5-Hydroxymethylfurfural Coupled with Hydrogen Generation. Acta Physico-Chimica Sinica, 2024, 40(9): 2306007-0. doi: 10.3866/PKU.WHXB202306007
15. [15]
  Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO₂ mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398
16. [16]
  Fangxuan Liu , Ziyan Liu , Guowei Zhou , Tingting Gao , Wenyu Liu , Bin Sun . 中空结构光催化剂. Acta Physico-Chimica Sinica, 2025, 41(7): 100071-0. doi: 10.1016/j.actphy.2025.100071
17. [17]
  Yichang Liu , Li An , Dan Qu , Zaicheng Sun . “双碳”背景下的综合设计实验——以PbCrO₄催化甲基蓝的光降解速率常数测定为例. University Chemistry, 2025, 40(6): 222-229. doi: 10.12461/PKU.DXHX202407105
18. [18]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
19. [19]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
20. [20]
  Yu Peng , Jiawei Chen , Yue Yin , Yongjie Cao , Mochou Liao , Congxiao Wang , Xiaoli Dong , Yongyao Xia . Tailored cathode electrolyte interphase via ethylene carbonate-free electrolytes enabling stable and wide-temperature operation of high-voltage LiCoO₂. Acta Physico-Chimica Sinica, 2025, 41(8): 100087-0. doi: 10.1016/j.actphy.2025.100087

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(592)
HTML views(29)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return