Synthesis of γ-Butyrolactone from trans-Cinnamaldehyde and Methyl p-Formylbenzoate Catalyzed by Thermoregulated Thiazolium Chiral Ionic Liquid

doi:10.6023/cjoc201311031

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (6): 1190-1195.DOI: 10.6023/cjoc201311031 Previous Articles Next Articles

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噻唑基温控手性离子液体催化反式肉桂醛和对甲酰基苯甲酸甲酯合成γ-丁内酯

于凤丽^a,b, 窦有涛^a, 赵冬梅^a, 解从霞^a, 于世涛^c

a. 青岛科技大学化学与分子工程学院青岛 266042;
b. 大连理工大学精细化工国家重点实验室大连 116024;
c. 青岛科技大学化工学院青岛 266042

收稿日期:2013-11-18 修回日期:2014-01-20 发布日期:2014-02-12
通讯作者: 解从霞 E-mail:xiecongxia@126.com
基金资助:
国家自然科学基金（No. 21006055）和大连理工大学精细化工国家重点实验室开放课题基金（No. KF1106）资助项目.

Synthesis of γ-Butyrolactone from trans-Cinnamaldehyde and Methyl p-Formylbenzoate Catalyzed by Thermoregulated Thiazolium Chiral Ionic Liquid

Yu Fengli^a,b, Dou Youtao^a, Zhao Dongmei^a, Xie Congxia^a, Yu Shitao^c

a. College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042;
b. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024;
c. College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042

Received:2013-11-18 Revised:2014-01-20 Published:2014-02-12
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21006055) and the State Key Laboratory of Fine Chemicals (No. KF1106).

From L-menthol, 5-(2-hydroxyethyl)-4-methylthiazole, paraformaldehyde and epoxyethane, a novel thermoregulated thiazolium chiral ionic liquid was synthesized and used for catalyzing the reaction of trans-cinnamaldehyde with methyl p-formylbenzoate to stereoselectively synthesize γ-butyrolactones with two chiral centres. By using the thermoregulation of the catalyst, the catalytic reaction in the thermoregulated solvent had the feature of "Thermoregulated Phase-separable Catalysis", and the recycling of the ionic liquid catalyst was easily achieved. THF/n-hexane (V:V=2.5:2) mixed solvent was selected as the thermoregulated solvent. Under the conditions of 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) as the alkaline reagent, the quantity of catalyst 10 mol%, the reaction temperature 35 ℃, and the reaction time 16 h, the conversion of trans-cinnamaldehyde could reach 95.4%, and the selectivity of γ-butyrolactones was 80.4%. The ratio of cis/trans product was 3.3, and the ee values of cis-product and trans-product were 21.3% and 16.1%, respectively. The recycling efficiency of the ionic liquid catalyst was investigated. During the recycles of 4 times, the catalytic activity of the ionic liquid was nearly unchanged.

Key words: ionic liquid, thermoregulated phase-separable catalysis, trans-cinnamaldehyde, γ-butyrolactone

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Yu Fengli, Dou Youtao, Zhao Dongmei, Xie Congxia, Yu Shitao. Synthesis of γ-Butyrolactone from trans-Cinnamaldehyde and Methyl p-Formylbenzoate Catalyzed by Thermoregulated Thiazolium Chiral Ionic Liquid[J]. Chin. J. Org. Chem., 2014, 34(6): 1190-1195.

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噻唑基温控手性离子液体催化反式肉桂醛和对甲酰基苯甲酸甲酯合成γ-丁内酯

Synthesis of γ-Butyrolactone from trans-Cinnamaldehyde and Methyl p-Formylbenzoate Catalyzed by Thermoregulated Thiazolium Chiral Ionic Liquid

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