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Authors: Selt, Maximilian
Gleede, Barbara
Franke, Robert
Stenglein, Andreas
Waldvogel, Siegfried R.
Title: Electrosynthesis of 3,3′,5,5’-tetramethyl-2,2′-biphenol in flow
Online publication date: 19-May-2021
Year of first publication: 2021
Language: english
Abstract: 3,3′,5,5’-Tetramethyl-2,2′-biphenol is well known as an outstanding building block for ligands in transition-metal catalysis and is therefore of particular industrial interest. The electro-organic method is a powerful, sustainable, and efficient alternative to conventional synthetic approaches to obtain symmetric and non-symmetric biphenols. Here, we report the successive scale-up of the dehydrogenative anodic homocoupling of 2,4-dimethylphenol (4) from laboratory scale to the technically relevant scale in highly modular narrow gap flow electrolysis cells. The electrosynthesis was optimized in a manner that allows it to be easily adopted to different scales such as laboratory, semitechnical and technical scale. This includes not only the synthesis itself and its optimization but also a work-up strategy of the desired biphenols for larger scale. Furthermore, the challenges such as side reactions, heat development and gas evolution that arose during optimization are also discussed in detail. We have succeeded in obtaining yields of up to 62% of the desired biphenol.
DDC: 540 Chemie
540 Chemistry and allied sciences
Institution: Johannes Gutenberg-Universität Mainz
Department: FB 09 Chemie, Pharmazie u. Geowissensch.
Place: Mainz
Version: Published version
Publication type: Zeitschriftenaufsatz
License: CC BY
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Journal: Journal of Flow Chemistry
Pages or article number: 143
Publisher: Springer Verlag
Issue date: 2021
ISSN: 2063-0212
Publisher URL:
Publisher DOI: 10.1007/s41981-020-00121-6
Appears in collections:JGU-Publikationen

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