Esterification or Thioesterification of Carboxylic Acids with Alcohols or Thiols Using Amphipathic Monolith-SO3H Resin

• Fumika Wakayama

  Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196 , Japan

• Ryo Ito

  Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196 , Japan

• Kwihwan Park

  Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196 , Japan

• Moeka Ishida

  Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196 , Japan

• Yutaro Yamada

  Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196 , Japan

• Shuta Ichihara

  Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196 , Japan

• Hitoshi Takada

  R & D Center, Organo Corporation, 4-4-1 Nishionuma, Minami-Ku, Sagamihara, Kanagawa 252-0332 , Japan

• Shinji Nakamura

  R & D Center, Organo Corporation, 4-4-1 Nishionuma, Minami-Ku, Sagamihara, Kanagawa 252-0332 , Japan

• Ayumu Kato

  R & D Center, Organo Corporation, 4-4-1 Nishionuma, Minami-Ku, Sagamihara, Kanagawa 252-0332 , Japan

• Tsuyoshi Yamada

  Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196 , Japan

• Hironao Sajiki

  Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196 , Japan

• Yasunari Monguchi

  Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196 , Japan

Abstract

We have developed a method for the esterification of carboxylic acids with alcohols using amphipathic, monolithic-resin bearing sulfonic acid moieties as cation exchange functions (monolith-SO3H). Monolith-SO3H efficiently catalyzed the esterification of aromatic and aliphatic carboxylic acids with various primary and secondary alcohols (1.5–5.0 equiv) in toluene at 60–80 °C without the need to remove water generated during the reaction. The amphipathic property of monolith-SO3H facilitates dehydration due to its capacity for water absorption. This reaction was also applicable to thioesterification, wherein the corresponding thioesters were obtained in excellent yield using only 2.0 equiv of thiol in toluene, although heating at 120 °C was required. Moreover, monolith-SO3H was separable from the reaction mixtures by simple filtration and reused for at least five runs without decreasing the catalytic activity.

Journal

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 94 (11), 2702-2710, 2021-10-01

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360290548663515776
• NII Article ID: 130008137554
• DOI: 10.1246/bcsj.20210266
• ISSN: 13480634
• ISSN: 00092673
• Web Site: https://academic.oup.com/bcsj/article-pdf/94/11/2702/56312727/bcsj.20210266.pdf
• Data Source:
  • Crossref
  • CiNii Articles
  • KAKEN