Oxidation of Eugenol Derivatives with KMnO4 and CrO3

Synthesis Pub Date : 2024-08-05 DOI:10.1055/s-0043-1775032
Achraf Abdou, Fatima Ezzahra Maaghloud, Nikolay Tumanov, Johan Wouters, Jamal JamalEddine, Abdelhakim Elmakssoudi, Mohamed Dakir
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Abstract

This study aims to delineate the synthesis of eugenol derivatives, starting with hydroxyl group protection and then the subsequent oxidation stages. Initially, eugenol underwent conversion into acetyleugenol and benzyleugenol during the protection phase. Subsequently, a kinetic oxidation of acetyleugenol with KMnO4 via GC-MS analysis resulted in the identification of four compounds. The kinetic investigation indicated the primary formation of diolacetyleugenol, succeeded by aldehyde eugenol, which further gets converted into its respective carboxylic acid. Additionally, acetyleugenol and benzyleugenol underwent oxidation with CrO3, yielding the corresponding carboxylic acids.

Abstract Image

用 KMnO4 和 CrO3 氧化丁香酚衍生物
本研究旨在阐述丁香酚衍生物的合成过程,首先是羟基保护阶段,然后是氧化阶段。首先,丁香酚在保护阶段转化为乙酰丁香酚和苄基丁香酚。随后,用 KMnO4 对乙酰丁香酚进行动力学氧化,并通过气相色谱-质谱分析鉴定出四种化合物。动力学研究表明,乙酰丁香酚主要生成二乙酰丁香酚,然后生成醛基丁香酚,再进一步转化为相应的羧酸。此外,乙酰丁香酚和苄基丁香酚与 CrO3 发生氧化反应,生成相应的羧酸。
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