Please use this identifier to cite or link to this item: https://doi.org/10.1002/cssc.201801340
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dc.titleA Dual-Functional Catalyst for Cascade Meerwein-Pondorf-Verley Reduction and Dehydration of 4 '-Methoxypropiophenone to Anethole
dc.contributor.authorZhang, Hongwei
dc.contributor.authorLim, Candy Li-Fen
dc.contributor.authorZaki, Muhammad
dc.contributor.authorJaenicke, Stephan
dc.contributor.authorChuah, Gaik Khuan
dc.date.accessioned2019-06-07T02:03:49Z
dc.date.available2019-06-07T02:03:49Z
dc.date.issued2018-09-11
dc.identifier.citationZhang, Hongwei, Lim, Candy Li-Fen, Zaki, Muhammad, Jaenicke, Stephan, Chuah, Gaik Khuan (2018-09-11). A Dual-Functional Catalyst for Cascade Meerwein-Pondorf-Verley Reduction and Dehydration of 4 '-Methoxypropiophenone to Anethole. CHEMSUSCHEM 11 (17) : 3007-3017. ScholarBank@NUS Repository. https://doi.org/10.1002/cssc.201801340
dc.identifier.issn1864-5631
dc.identifier.issn1864-564X
dc.identifier.urihttps://scholarbank.nus.edu.sg/handle/10635/155379
dc.description.abstract© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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.
dc.language.isoen
dc.publisherWILEY-V C H VERLAG GMBH
dc.sourceElements
dc.subjectScience & Technology
dc.subjectPhysical Sciences
dc.subjectChemistry, Multidisciplinary
dc.subjectGreen & Sustainable Science & Technology
dc.subjectChemistry
dc.subjectScience & Technology - Other Topics
dc.subjectdomino reactions
dc.subjectheterogeneous catalysis
dc.subjectlewis acids
dc.subjecthydrogenation
dc.subjectzirconium
dc.subjectFENNEL FOENICULUM-VULGARE
dc.subjectSUPERCRITICAL-FLUID EXTRACTION
dc.subjectESSENTIAL OIL COMPOSITION
dc.subjectPIMPINELLA-ANISUM L.
dc.subjectZR-ZEOLITE BETA
dc.subjectMESOPOROUS SILICA
dc.subjectHETEROGENEOUS CATALYST
dc.subjectCHEMICAL-COMPOSITION
dc.subjectMOLECULAR-SIEVES
dc.subjectGREEN CHEMISTRY
dc.typeArticle
dc.date.updated2019-06-04T02:15:48Z
dc.contributor.departmentCHEMISTRY
dc.description.doi10.1002/cssc.201801340
dc.description.sourcetitleCHEMSUSCHEM
dc.description.volume11
dc.description.issue17
dc.description.page3007-3017
dc.published.statePublished
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