Synthesis 2008(14): 2303-2306  
DOI: 10.1055/s-2008-1067145
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

2,5-Dihydroxyterephthalates, 2,5-Dichloro-1,4-benzoquinone-3,6-dicarbox­ylates, and Polymorphic 2,5-Dichloro-3,6-dihydroxyterephthalates

Lukas Hintermann, Keisuke Suzuki*
Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan
Fax: +81(3)57342788; e-Mail: ksuzuki@chem.titech.ac.jp;
Further Information

Publication History

Received 7 May 2008
Publication Date:
18 June 2008 (online)

Abstract

Reaction of 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylates with one equivalent of N-chlorosuccinimide cleanly gives 2,5-dihydroxyterephthalates; reaction with four equivalents of N-chlorosuccinimide gives 2,5-dichloro-1,4-benzoquinone-3,6-dicarboxylates instead. The latter compounds react with sodium dithionite to give 2,5-dichloro-3,6-dihydroxyterephthalates, which will find use in the study of polymorphic phase changes.

1

Current address: L. Hintermann, Institute of Organic Chemistry, RWTH, Aachen, Germany.