Convenient one-pot synthesis of 2,2-bis-(4-hydroxyphenyl)-cyclopentanone

Jai Seo, Jun Kim Hee, Se Lee Byoung, John A. Katzenellenbogen, Yoon Chi Dae

Research output: Contribution to journalArticle

23 Scopus citations

Abstract

(Chemical Equation Presented) 2,2-Bis-(4-hydroxyphenyl)-cyclopentanone (3a) was unexpectedly obtained in 76% yield from a reductive coupling reaction of 4,4′-dihydroxybenzophenone (1a) and cyclobutanone with TiCl4 and Zn. Further optimization showed that catechol as an external ligand and a hydroxy group on benzophenone facilitated the generation of a quinonemethide (intermediate II) that is involved in the pinacol-type rearrangement of intermediate I to give the rearranged product.

Original languageEnglish (US)
Pages (from-to)715-718
Number of pages4
JournalJournal of Organic Chemistry
Volume73
Issue number2
DOIs
StatePublished - Jan 18 2008
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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    Seo, J., Hee, J. K., Byoung, S. L., Katzenellenbogen, J. A., & Dae, Y. C. (2008). Convenient one-pot synthesis of 2,2-bis-(4-hydroxyphenyl)-cyclopentanone. Journal of Organic Chemistry, 73(2), 715-718. https://doi.org/10.1021/jo701850u