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

A continuous flow process was optimized 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. A yield of 200 g of pure material was furnished within 5 hours of operation (throughput = 40 g h⁻¹). The compound was easily isolated by filtration and was obtained with 95% purity, as determined by GC analysis. Further purification was carried out by crystallization from a 20:1 Hexane/AcOEt mixture left at −20 °C overnight. Characterization of the resultant product was performed using ¹H and ¹³C NMR, MS, and IR analyses, with melting point and X-ray single-crystal data also being obtained to confirm the structure.

• Gambacorta, G
• Teo, Q
• Baxendale, I

• Department of Chemistry, University of Durham, South Road, Durham DH1 3LE, UK

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