Synlett 2013; 24(19): 2614-2615
DOI: 10.1055/s-0033-1338976
© Georg Thieme Verlag Stuttgart · New York


Zahra Tanbakouchian
Catalysis and Peptide Research Unit, School of Health Sciences, University of KwaZulu-Natal, Durban 4001, South Africa   Email:
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Publication History

Publication Date:
18 September 2013 (online)


Hexachlorocyclohexa-2,5-dien-1-one is informally called hexachlorophenol (HCP). It is an efficient reagent for the chlorination of a wide variety of compounds and was used in several chiral organocatalytic reactions. HCP is a yellow to brown crystalline solid, which is usually prepared via electrophilic chlorination of phenol by chlorine gas in the presence of a metal chloride catalyst, such as iron(III) chloride.[1]

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Scheme 1
  • References

  • 1 Gali S, Miravitlles C, Font-Altaba M. Acta Cryst. 1975; B31: 2510
  • 2 Butler JR, Wang C, Bian J, Ready JM. J. Am. Chem. Soc. 2011; 133: 9956
  • 3 Duan XH, Mayr H. Org. Lett. 2010; 12: 2238
    • 4a Wack H, Taggi AE, Hafez AM, Drury WJ, Lectka T. J. Am. Chem. Soc. 2001; 123: 1531
    • 4b Taggi AE, Wack H, Hafez AM, France S, Lectka T. Org. Lett. 2002; 4: 627
    • 4c Dogo-Isonagie C, Bekele T, France S, Wolfer J, Weatherwax A, Taggi AE, Paull DH, Dudding T, Lectka T. Eur. J. Org. Chem. 2007; 1091
  • 5 France S, Wack H, Taggi AE, Hafez AM, Wagerle TR, Shah MH, Dusich CL, Lectka T. J. Am. Chem. Soc. 2004; 126: 4245
  • 6 Sparr C, Gilmour R. Angew. Chem. Int. Ed. 2011; 50: 8391
  • 7 Brochu MP, Brown SP, MacMillan DW. C. J. Am. Chem. Soc. 2004; 126: 4108
  • 8 Huang Y, Walji AM, Larsen CH, MacMillan DW. C. J. Am. Chem. Soc. 2005; 127: 15051
  • 9 Douglas J, Ling KB, Concellón C, Churchill G, Slawin AM. Z, Smith AD. Eur. J. Org. Chem. 2010; 5863