Synthesis 2004(15): 2591-2593  
DOI: 10.1055/s-2004-829194
PSP
© Georg Thieme Verlag Stuttgart · New York

Preparation of 5- and 6-Carboxyfluorescein

Yuichiro Ueno, Guan-Sheng Jiao, Kevin Burgess*
Department of Chemistry, Texas A & M University, P.O. Box 30012, College Station, Texas 77842, USA
Fax: 001(979)8458839; e-Mail: [email protected];
Further Information

Publication History

Received 3 March 2004
Publication Date:
13 August 2004 (online)

Abstract

Condensation of resorcinol with 4-carboxyphthalic anhydride in methanesulfonic acid gave a mixture of 5- and 6-carboxyfluorescein stereoisomers. These were separated by recrystallization from methanol- or ethanol-hexane to give 5- and 6-carboxyfluorescein, each in over 98% purity.

    References

  • 1 Orndorff WR. Hemmer AJ. J. Am. Chem. Soc.  1927,  49:  1272 
  • 2 Adamczyk M. Fishpaugh JR. Heuser KJ. Bioconjugate Chem.  1997,  8:  253 
  • 3 Adamczyk M. Chan CM. Fino JR. Mattingly PG. J. Org. Chem.  2000,  65:  596 
  • 4 Fischer R. Mader O. Jung G. Brock R. Bioconjugate Chem.  2003,  14:  653 
  • 5 Lyttle MH. Carter TG. Cook RM. Org. Process Res. Dev.  2001,  5:  45 
  • 6 Sun W.-C. Gee KR. Klaubert DH. Haugland RP. J. Org. Chem.  1997,  62:  6469 
  • 7 Jiao G.-S. Han JW. Burgess K. J. Org. Chem.  2003,  68:  8264 
  • 8 Rossi FM. Kao JPY. Bioconjugate Chem.  1997,  8:  495