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A Dual‐Functional Catalyst for Cascade Meerwein–Pondorf–Verley Reduction and Dehydration of 4′‐Methoxypropiophenone to Anethole
ChemSusChem ( IF 8.4 ) Pub Date : 2018-07-23 , DOI: 10.1002/cssc.201801340 Hongwei Zhang 1 , Candy Li-Fen Lim 1 , Muhammad Zaki 1 , Stephan Jaenicke 1 , Gaik Khuan Chuah 1
ChemSusChem ( IF 8.4 ) Pub Date : 2018-07-23 , DOI: 10.1002/cssc.201801340 Hongwei Zhang 1 , Candy Li-Fen Lim 1 , Muhammad Zaki 1 , Stephan Jaenicke 1 , Gaik Khuan Chuah 1
Affiliation
Anethole is an ingredient in many flavours, fragrances and pharmaceutical formulations. To reduce the dependence of its supply on natural oils, a green route for anethole synthesis was designed on the basis of Meerwein–Pondorf–Verley (MPV) reduction and dehydration of 4′‐methoxypropiophenone. The one‐pot cascade reactions were heterogeneously catalysed by dual‐functional Zr‐MSU‐3, a predominantly Lewis‐acidic catalyst with a Si/Zr ratio of 10 and pores with sizes in the range of 3.2–4.2 nm. The use of 2‐pentanol as solvent and hydrogen donor for the MPV reduction was advantageous, as its high boiling point enhances the rate of the reactions, especially the dehydration of the MPV product, 1‐(4‐methoxyphenyl)‐propan‐1‐ol. This dispenses with the need for a strong acid catalyst that could result in by‐products of acid‐catalysed reactions. Anethole yields of 91 % with a trans/cis isomer ratio of about 92:8, similar to that of natural anethole, were obtained. In comparison, microporous Zr‐beta (Si/Zr 12.5) gave lower activity owing to pore‐size constraints. Hence, through design of the reactions and catalyst, 4′‐methoxypropiophenone can be efficiently converted to anethole in a sustainable and green manner.
中文翻译:
级联Meerwein-Pondorf-Verley还原和脱水4'-甲氧基苯乙酮成茴香脑的双功能催化剂
茴香脑是许多调味剂,香料和药物制剂中的成分。为了减少其对天然油的依赖,在Meerwein-Pondorf-Verley(MPV)还原和脱水4'-甲氧基丙苯酮的基础上,设计了茴香脑合成的绿色路线。单锅级联反应是由双功能Zr-MSU-3(一种主要的路易斯酸性催化剂,Si / Zr之比为10)和孔径在3.2-4.2 nm范围内的多相催化剂催化的。使用2-戊醇作为溶剂和氢供体可降低MPV,因为其高沸点可提高反应速率,尤其是MPV产物1-(4-甲氧基苯基)-丙烷-1-的脱水反应。 ol。这就消除了对强酸催化剂的需求,这种强酸催化剂可能会导致酸催化反应的副产物。获得的反式/顺式异构体比例约为92:8,与天然茴香脑相似。相比之下,由于孔径限制,微孔Zr-β(Si / Zr 12.5)的活性较低。因此,通过反应和催化剂的设计,可以以可持续和绿色的方式将4'-甲氧基丙苯酮有效地转化为茴香脑。
更新日期:2018-07-23
中文翻译:
级联Meerwein-Pondorf-Verley还原和脱水4'-甲氧基苯乙酮成茴香脑的双功能催化剂
茴香脑是许多调味剂,香料和药物制剂中的成分。为了减少其对天然油的依赖,在Meerwein-Pondorf-Verley(MPV)还原和脱水4'-甲氧基丙苯酮的基础上,设计了茴香脑合成的绿色路线。单锅级联反应是由双功能Zr-MSU-3(一种主要的路易斯酸性催化剂,Si / Zr之比为10)和孔径在3.2-4.2 nm范围内的多相催化剂催化的。使用2-戊醇作为溶剂和氢供体可降低MPV,因为其高沸点可提高反应速率,尤其是MPV产物1-(4-甲氧基苯基)-丙烷-1-的脱水反应。 ol。这就消除了对强酸催化剂的需求,这种强酸催化剂可能会导致酸催化反应的副产物。获得的反式/顺式异构体比例约为92:8,与天然茴香脑相似。相比之下,由于孔径限制,微孔Zr-β(Si / Zr 12.5)的活性较低。因此,通过反应和催化剂的设计,可以以可持续和绿色的方式将4'-甲氧基丙苯酮有效地转化为茴香脑。