Please use this identifier to cite or link to this item: https://doi.org/10.1002/cssc.201801340
Title: A Dual-Functional Catalyst for Cascade Meerwein-Pondorf-Verley Reduction and Dehydration of 4 '-Methoxypropiophenone to Anethole
Authors: Zhang, Hongwei 
Lim, Candy Li-Fen
Zaki, Muhammad
Jaenicke, Stephan 
Chuah, Gaik Khuan 
Keywords: Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Green & Sustainable Science & Technology
Chemistry
Science & Technology - Other Topics
domino reactions
heterogeneous catalysis
lewis acids
hydrogenation
zirconium
FENNEL FOENICULUM-VULGARE
SUPERCRITICAL-FLUID EXTRACTION
ESSENTIAL OIL COMPOSITION
PIMPINELLA-ANISUM L.
ZR-ZEOLITE BETA
MESOPOROUS SILICA
HETEROGENEOUS CATALYST
CHEMICAL-COMPOSITION
MOLECULAR-SIEVES
GREEN CHEMISTRY
Issue Date: 11-Sep-2018
Publisher: WILEY-V C H VERLAG GMBH
Citation: Zhang, 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
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.
Source Title: CHEMSUSCHEM
URI: https://scholarbank.nus.edu.sg/handle/10635/155379
ISSN: 1864-5631
1864-564X
DOI: 10.1002/cssc.201801340
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