A Study on the Synthesis of Veratraldehyde

Hu Kai; Dong Jie; Li Xiang; Li Dong; Zhao Yu Xiang; Zhu Yan Ren; Wang Jing; Liu Dan Dan; Zhou Lin Zong; Liang Lei Lei; Chen Jing Bo

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Article Navigation > Journal of Kunming Medical University > 2018 > 39(06): 31-34

Hu Kai , Dong Jie , Li Xiang , Li Dong , Zhao Yu Xiang , Zhu Yan Ren , Wang Jing , Liu Dan Dan , Zhou Lin Zong , Liang Lei Lei , Chen Jing Bo . A Study on the Synthesis of Veratraldehyde[J]. Journal of Kunming Medical University, 2018, 39(06): 31-34.

Citation:

Hu Kai , Dong Jie , Li Xiang , Li Dong , Zhao Yu Xiang , Zhu Yan Ren , Wang Jing , Liu Dan Dan , Zhou Lin Zong , Liang Lei Lei , Chen Jing Bo . A Study on the Synthesis of Veratraldehyde[J]. Journal of Kunming Medical University, 2018, 39(06): 31-34.

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A Study on the Synthesis of Veratraldehyde

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基金：国家自然科学基金资助项目 (21662041); 云南省科技厅-昆明医科大学应用基础研究联合专项基金资助项目[2017FE468 (-022) ]; 云南省天然药物药理重点实验室开放研究基金资助项目 (YZDY1501); 云南省教育厅科学研究基金资助项目 (2017zzx196);

Received Date: 2018-01-16

Abstract

Abstract

Objective Veratraldehyde is an important pharmaceutical intermediate and chemical raw material. Taking common synthetic methods of Veratraldehyde into consideration, the study is aimed to further investigate a more efficient synthetic route in order to provide a solid foundation for the application of Veratraldehyde.Me thods This article introduces an alternative method based on the Triton-B catalyzed olefin isomerization of methyl Eugenol followed by ozonation/reduction reaction.Re s ults In the experiment, the optimal conditions was selected by investigating the influence of reaction time, reaction temperature and catalyst dosage on the yield of Veratraldehyde. The total yield of this 2-step reactions was 64%. Conclus ion The above-mentioned synthesis method only requires raw materials that are easily acquired and its relative reaction conditions are mild, thus it will provide values in the industrial applications.
- Veratraldehyde,
- Synthesis,
- Olefin isomerization,
- Ozonation/reduction

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References(17)

References

[1]王庆全, 林阿利, 唐伟.哌唑嗪的合成路线[J].黑龙江医药, 2002, 15 (4) :268-269.
[2]孔荣祖, 方成林, 华维一.藜芦心胺的合成[J].南京药学院学报, 1984, 15 (2) :53-54.
[3]王湛, 贾俐萍, 计志忠.利喘贝合成工艺的改革[J].沈阳药科大学学报, 1986, 3 (1) :44-46.
[4]刘福胜, 李英春, 于世涛.相转移催化法合成3, 4-二甲氧基苯甲醛[J].精细化工, 2002, 19 (12) :741-743.
[5]钱正强, 周金江, 杨明挚.不同年龄香桂叶精油含量及成分差异分析[J].云南大学学报 (自然科学版) , 2009, 31 (S2) :464-467.
[6]刘娜, 张娜, 夏沙.藏药革叶兔耳草化学成分的研究[J].云南大学学报 (自然科学版) , 2015, 37 (2) :272-278.
[7]李来伟, 杨姝, 羊晓东.剑叶木姜子的化学成分研究[J].云南大学学报 (自然科学版) , 2008, 30 (2) :187-190.
[8]徐冰凌.藜芦醛的合成及应用[J].精细化工中间体, 1998, 28 (4) :11-13.
[9]王成峰, 林原斌.Vilsmeier法合成3, 4-二甲氧基苯甲醛的研究[J].电力科学与技术学报, 2004, 19 (4) :87-88.
[10]刘铸晋, 甘立宪.从甲基丁香酚合成藜芦醛[J].有机化学, 1980, 5 (4) :36-37.
[11]	[11]MATSJEH S, ANWAR C, SHOLIKHAH E N.Synthesis3, 4-Dimethoxybenzyl-2, 4-Di-hydroxyphenyl Ketone from Eugenol[J].International Journal of Chemical Engineering&Applications, 2015, 6 (1) :61-65.
[12]	[12]AL-MASKERY I, GIRLING K, JACKSON S D.High Activity Solid Base Catalysts for Alkenyl Aromatic Isomerisation[J].Topics in Catalysis, 2010, 53 (15-18) :1163-1165.
[13]	[13]LUU T X, LAM T T, LE T N.Fast and green microwave-assisted conversion of essential oil allylbenzenes into the corresponding aldehydes via alkene isomerization and subsequent potassium permanganate promoted oxidative alkene group cleavage[J].Molecules, 2009, 14 (9) :3411-3424.
[14]	[14]LARSEN C R, PAULSON E R, ERDOGAN G.Chem Inform abstract:A facile, convenient, and green route to (E) propenylbenzene flavors and fragrances by alkene isomerization[J].Synlett, 2015, 26 (17) :2462-2466.
[15]	[15]SHARMA U K, SOOD S, SHARMA N.Synthesis and SAR investigation of natural phenylpropene-derived methoxylatedcinnamaldehydes and their novel Schiff bases as potent antimicrobial and antioxidant agents[J].Medicinal Chemistry Research, 2013, 22 (11) :5129-5140.
[16]	[16]LAI B, HUANG Z, JIA Z.Silica-supported metal acetylacetonate catalysts with a robust and flexible linker constructed by using 2-butoxy-3, 4-dihydropyrans as dual anchoring reagents and ligand donors[J].Catalysis Science&Technology, 2016, 6 (6) :1810-1820.
[17]诸富根, 周山花, 冯雪峰.异丁香酚连续臭氧氧化制备香兰素研究[J].香料香精化妆品, 2000, 27 (3) :13-16.

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