Advanced approach to O-alkyl/aryl salicylaldehyde derivatives: Synthesis, characterization, and free-radical homopolymerization for improved thermal stability
In the development of bioactive materials centered around salicylaldehyde, we synthesized O-alkyl/aryl derivatives through the etherification of the phenolic group. Salicylaldehyde underwent a copper-catalyzed reaction with various halides under basic conditions, yielding 2-(3-chloropyrazin-2-yl)oxy...
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| Main Authors: | , |
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| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2025-06-01
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| Series: | Tetrahedron Green Chem |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2773223125000111 |
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| Summary: | In the development of bioactive materials centered around salicylaldehyde, we synthesized O-alkyl/aryl derivatives through the etherification of the phenolic group. Salicylaldehyde underwent a copper-catalyzed reaction with various halides under basic conditions, yielding 2-(3-chloropyrazin-2-yl)oxy benzaldehyde, 2-(6-chloropyrimidin-4-yl)oxy benzaldehyde, and 3-(2-formylphenoxy)-2-hydroxypropyl methacrylate. Meanwhile, 2-(2-formylphenoxy)ethyl methacrylate was synthesized via a sonication-assisted Mitsunobu reaction, affording high yields of ether derivatives. Structural elucidation was achieved using standard analytical techniques, such as 1H NMR, 13C NMR, FT-IR and LC-MS. The free radical homopolymerization of 3-(2-formylphenoxy)-2-hydroxypropyl methacrylate using benzoyl peroxide as an initiator was successfully achieved. The resulting polymer exhibited enhanced thermal stability, as confirmed by solid-state 13C NMR, FT-IR, TGA, DSC, and SEM analyses, with a higher glass transition temperature than the reported poly(glycidyl methacrylate). This increase in Tg is attributed to the enhanced rigidity introduced by the aromatic ring in the homopolymer. This study highlights the successful synthesis of various O-alkyl/aryl salicylaldehyde derivatives using different techniques and functionalities, followed by the effective polymerization of one of the monomers, 3-(2-formylphenoxy)-2-hydroxypropyl methacrylate. |
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| ISSN: | 2773-2231 |