A method for preparing deuterium-labeled 4-alkylphenol compounds

CN117603019BActive Publication Date: 2026-05-26ALTA (TIANJIN) REFERENCE MATERIALS RES INST CO LTD +1
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
ALTA (TIANJIN) REFERENCE MATERIALS RES INST CO LTD
Filing Date
2023-11-23
Publication Date
2026-05-26

AI Technical Summary

Technical Problem

Existing technologies are difficult to synthesize deuterated alkylphenol compounds for isotope dilution mass spectrometry efficiently, and existing methods are costly and produce a mixture of branched isomers, which is not suitable for the widespread application of internal standard reagents.

Method used

A method for synthesizing deuterium-labeled 4-alkylphenol compounds was designed. Deuterium-labeled atoms were introduced at specific sites through DH exchange and deuteration reduction. Multiple chemical reaction routes were adopted, including metal-catalyzed coupling, DH exchange, cyano hydrolysis and esterification, to selectively synthesize target products with different deuteration rates.

Benefits of technology

The synthesis of deuterium-labeled products of various common 4-position substituted alkylphenols was achieved. The target compounds were selectively labeled with deuterium on the aromatic ring skeleton and branches, which expanded the application scenarios. The products had high isotopic abundance, were easy to obtain, and avoided isotopic dilution.

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Abstract

This invention provides a method for preparing deuterium-labeled 4-alkylphenol compounds, enabling the synthesis of deuterium-labeled products of various common 4-substituted alkylphenols, such as deuterium-labeled nonylphenol and deuterium-labeled octylphenol. The method is novel, and all deuterium-labeled intermediates involved in the design are new compounds. This method successfully achieves directional deuteration substitution of hydrogen atoms on saturated carbon chains through D-H exchange (deuterium hydrogen exchange) and deuteration reduction. By adjusting the synthesis strategy, such as selectively using deuterium-labeled reducing agents or ordinary reducing agents, and selectively executing the D-H exchange step, target products with different labeling units, such as D4, D6, and D8, can be selectively obtained. The products can be used not only for the quantitative detection of the main alkylphenol component but also for the quantitative detection of its metabolic fragments.
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