Lactamomethylation of alkylphenols: synthesis and quantum-chemical study of the reaction pathway

Vorobyev, Stepan V.; Primerova, Olga V.; Bylikin, Sergey Yu. and Koshelev, Vladimir N. (2021). Lactamomethylation of alkylphenols: synthesis and quantum-chemical study of the reaction pathway. Arabian Journal of Chemistry, 14(11), article no. 103424.

DOI: https://doi.org/10.1016/j.arabjc.2021.103424

Abstract

Six novel lactamomethyl derivatives of 2,5-dimethylphenol and 2,3,5-trimethylphenol were prepared with moderate yields by the reaction of corresponding phenols with 1-(hydroxymethyl)lactams in the presence of an acid catalyst. In all cases, the substitution occurred at position 4 to the phenolic hydroxyl group. The structures of all synthesized compounds were confirmed by FT-IR, ¹H and ¹³C NMR, 2D NMR and elemental analysis. The selectivity and possible pathways of the lactamomethylation reaction were studied by quantum-chemical methods. In silico calculations showed that the substitution at para-position to the hydroxyl group of the corresponding phenols was more preferable due to the higher stability of forming intermediates.

Viewing alternatives

Metrics

Item Actions

Export

You can export this page using these formats Digital Object Identifier - DOI