Formation of five-membered carbocycles from D-glucose: A Concise Synthesis of 4-Hydroxy-2-(hydroxymethyl)cyclopentenone

Yoshitaka Koseki, Toshihiro Watanabe, Takaaki Kamishima, Eunsang Kwon, Hitoshi Kasai

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

A concise synthesis of 4-hydroxy-2-(hydroxymethyl)cyclo-pentenone (1) has been accomplished from D-glucose by a three-step sequence that features a catalyst-free hydrothermal reaction of D-glucal, which is readily obtained from D-glucose. Optimization of the reaction conditions for synthesizing 1 was performed by changing the temperature and reaction time. The treatment of D-glucal under the optimal conditions, i.e., at 120 °C for 24 h, provided 1 in the highest isolated yield of 61%. 1 would become a versatile intermediate for the synthesis of various fine chemicals having a cyclopentenone structure from cellulosic biomass.

Original languageEnglish
Pages (from-to)1324-1328
Number of pages5
JournalBulletin of the Chemical Society of Japan
Volume92
Issue number8
DOIs
Publication statusPublished - 2019

Keywords

  • Biomass feedstock
  • Glucose conversion
  • Hydrothermal reaction

ASJC Scopus subject areas

  • Chemistry(all)

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