Convenient Preparative Method for Lactones from 3-hydroxy Propanoic Acids Using Iodine under Solvent-Free Conditions

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概要

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• Intramolecular cyclization of 3-hydroxy acids was investigated using iodine as a catalyst under solvent-free conditions. The reaction proceeded to completion in the heterogeneous system. Lactones were obtained by intramolecular cyclization of 3-hydroxy acids. Propella lactone (11-oxatricyclo[4.4.3.01,6]tridecan-12-one) was conveniently synthesized from 3-hydroxy acid ((6-hydroxyspiro[4.5]dec-6-yl)acetic acid) in 88% yield with carbon skeleton rearrangement. Spiro lactones and bicyclic lactones were also obtained from the corresponding 3-hydroxy acids in yields of over 75%. The most suitable reaction conditions were a temperature of 80°C, a molar ratio of 3-hydroxy acid:iodine = 1:0.1, and a time period of 6 h. In addition, terpenic lactones were efficiently synthesized from the corresponding 3-hydroxy acids, derived from (+)-camphor, (-)-fencone, and (-)-pulegone, with skeleton rearrangement. The yield of the solvent-free reaction was as high as that of the corresponding reaction in solution.

• 日本油化学会の論文

著者

• Mino Takashi

  Department Of Urban And Environmental Engineering University Of Tokyo

• FUJITA Tsutomu

  Department of Materials Technology, Faculty of Engineering, Chiba University

• Sakamoto Masami

  Graduate School Of Engineering Chiba Univ.

• Kasashima Yoshio

  Education center, Faculty of engineering, Chiba Institute of Technology

• Fujimoto Hiroshi

  Graduate School of Science and Technology, Chiba University

• Nishida Tadasuke

  Graduate School of Science and Technology, Chiba University

• Mino Takashi

  Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Chiba University

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