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Process for preparing 2, 2'-biphenols using selenium dioxide

A technology of selenium dioxide and biphenol, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc.

Inactive Publication Date: 2015-12-02
EVONIK OPERATIONS GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Especially when using multi-step sequences, different solvents need to be changed, which is cumbersome and implies an additional cost factor

Method used

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  • Process for preparing 2, 2'-biphenols using selenium dioxide
  • Process for preparing 2, 2'-biphenols using selenium dioxide
  • Process for preparing 2, 2'-biphenols using selenium dioxide

Examples

Experimental program
Comparison scheme
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Embodiment Construction

[0028] In one version of the process, the first phenol in process step a) is a compound of general formula I:

[0029]

[0030] where R 1 , R 2 , R 3 , R 4 , R 5 each independently selected from:

[0031] -H, -(C 1 -C 12 )-Alkyl, -O-(C 1 -C 12 )-Alkyl, -(C 6 -C 20 )-aryl, -O-(C 6 -C 20 )-aryl, halogen (such as Cl, F, Br, I), -OC=O-(C 1 -C 12 )-alkyl,

[0032] Two adjacent residues can also combine with each other to form a condensation system,

[0033] wherein said alkyl and aryl groups may be substituted,

[0034] and at least one R 1 or R 5 Equivalent to -H.

[0035] (C 1 -C 12 )-Alkyl and O-(C 1 -C 12 )-alkyl groups may in each case be unsubstituted or substituted by one or more identical or different residues selected from the group consisting of:

[0036] (C 3 -C 12 )-Cycloalkyl, (C 3 -C 12 )-Heterocycloalkyl, (C 6 -C 20 )-aryl, fluoro, chloro, cyano, formyl, acyl or alkoxycarbonyl.

[0037] (C 6 -C 20 )-aryl and O-(C 6 -C 20 )-aryl c...

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Abstract

A process for preparing a 2,2′-biphenol, proceeds by a) adding a first phenol to a reaction mixture, b) adding a second phenol to the reaction mixture, c) adding selenium dioxide to the reaction mixture, d) adding an acid having a pKa in the range from 0.0 to 5.0 to the reaction mixture, and e) heating the reaction mixture such that the first phenol and the second phenol are converted to said 2,2′-biphenol.

Description

technical field [0001] The present invention relates to a process for the preparation of 2,2'-biphenols using selenium dioxide. Background technique [0002] Direct coupling of phenols to their industrially important corresponding biphenol derivatives has always been a challenge, as these reactions are generally neither regioselective nor chemoselective. [0003] The term phenols is used in this application as a class term and thus also includes substituted phenols. [0004] These biphenols can especially be synthesized electrochemically. Carbon electrodes such as graphite, glassy carbon, BDD or noble metals such as platinum are used here (see F. Stecker, A. Fischer, I. M. Malkowsky, S. R. Waldvogel, A. Kirste, WO2010139687 A1 and A. Fischer, I. M. Malkowsky, F. Stecker, S. R. Waldvogel, A. Kirste WO2010023258A1). The disadvantage of these electrochemical methods is that some expensive devices have to be specially fabricated. In addition, scaling up to the ton-scale scal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/15C07C37/11C07C391/02
CPCC07C37/11C07C39/15C07C391/02
Inventor K·M·迪巴拉R·弗兰克D·弗里达格S·R·瓦尔德福格尔T·奎尔M·米里翁
Owner EVONIK OPERATIONS GMBH
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