112715-88-5Relevant academic research and scientific papers
Esterification or Thioesterification of Carboxylic Acids with Alcohols or Thiols Using Amphipathic Monolith-SO3H Resin
Ichihara, Shuta,Ishida, Moeka,Ito, Ryo,Kato, Ayumu,Monguchi, Yasunari,Nakamura, Shinji,Park, Kwihwan,Sajiki, Hironao,Takada, Hitoshi,Wakayama, Fumika,Yamada, Tsuyoshi,Yamada, Yutaro
, p. 2702 - 2710 (2022/01/19)
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 (1.55.0 equiv) in toluene at 6080 °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.
Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides
Guissart, Céline,Barros, Andre,Rosa Barata, Luis,Evano, Gwilherm
supporting information, p. 5098 - 5102 (2018/09/13)
An efficient, broadly applicable, operationally simple, and divergent process for the transformation of imides into a range of carboxylic acid derivatives under mild conditions is reported. By simply using catalytic amounts of ytterbium(III) triflate as a Lewis acid promoter in the presence of alcohols, water, amines, or N,O-dimethylhydroxylamine, a broad range of imides is smoothly and readily converted to the corresponding esters, carboxylic acids, amides, and Weinreb amides in good yields. This method notably enables an easy cleavage of oxazolidinone-based auxiliaries.
Catalytic Deprotection of Protected Alcohols in Water Using Low-Loading and Alkylated Polystyrene-Supported Sulfonic Acid
Iimura, Shinya,Manabe, Kei,Kobayashi, Shu
, p. 8723 - 8725 (2007/10/03)
Catalytic deprotection of various protected alcohols was efficiently conducted using a hydrophobic low-loading and alkylated polystyrene-supported sulfonic acid (LL-ALPS-SO3H) in water as the sole solvent. Transprotection of an alcohol from a silyl ether to the corresponding benzylic ether or ester also proceeded smoothly in water.
Dehydration reactions in water. Bronsted acid-surfactant-combined catalyst for ester, ether, thioether, and dithioacetal formation in water
Manabe, Kei,Iimura, Shinya,Sun, Xiang-Min,Kobayashi, Shu
, p. 11971 - 11978 (2007/10/03)
Dehydration reactions in water have been realized by a surfactant-type catalyst, dodecylbenzenesulfonic acid (DBSA). These reactions include dehydrative esterification, etherification, thioetherification, and dithioacetalization. In these reactions, DBSA and substrates form emulsion droplets whose interior is hydrophobic enough to exclude water molecules generated during the reactions. Detailed studies on the esterification revealed that the yields of esters were affected by temperature, amounts of DBSA used, and the substrates. Esters were obtained in high yields for highly hydrophobic substrates. On the basis of the difference in hydrophobicity of the substrates, unique selective esterification and etherification in water were attained. Furthermore, chemospecific, three-component reactions under DBSA-catalyzed conditions were also found to proceed smoothly. This work not only may lead to environmentally benign systems but also will provide a new aspect of organic chemistry in water.
