2,4,6-Trichloro-cyclohexa-2,5-dienone

Gambacorta, Guido; Teo, Qin Han; Baxendale, Ian R.

Abstract

A continuous flow process was optimised for the perchlorination of p-cresol to the corresponding 2,4,6-trichloro-cyclohexa-2,5-dienone derivative employing trichloroisocyanuric acid as a green and safer-to-handle chlorinating agent. The system could furnish 200 g of pure material within 5 h of operation (throughput = 40 g h−1). The compound was easily isolated by filtration and obtained in 95% purity as determined by GC analysis; it could be further purified by crystallisation from a 20:1 Hexane/AcOEt mixture left at −20 °C overnight. The resultant product was characterised by 1H & 13C NMR, MS, IR analyses, with melting point and X-ray single-crystal data being obtained, confirming the structure.

Citation

Gambacorta, G., Teo, Q. H., & Baxendale, I. R. (2025). 2,4,6-Trichloro-cyclohexa-2,5-dienone. Molbank, 2025(1), M1969. https://doi.org/10.3390/m1969

• Journal Article Type: Article
• Acceptance Date: Feb 13, 2025
• Online Publication Date: Feb 19, 2025
• Publication Date: Feb 19, 2025
• Deposit Date: Apr 2, 2025
• Publicly Available Date: Apr 2, 2025
• Journal: Molbank
• Electronic ISSN: 1422-8599
• Publisher: MDPI
• Peer Reviewed: Peer Reviewed
• Volume: 2025
• Issue: 1
• Article Number: M1969
• DOI: https://doi.org/10.3390/m1969
• Keywords: perchlorination, flow chemistry chlorinating agent, X-ray structure, scale-up, trichloroisocyanuric acid
• Public URL: https://durham-repository.worktribe.com/output/3714815