Open-air and solvent-free ester condensation catalyzed by sulfonic acids

Akira Sakakura, Yoshiki Koshikari, Kazuaki Ishihara

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Ester condensation is one among the most fundamental organic transformations, and more environmentally benign alternatives to current esterification processes are needed. Under solvent-free and drying agent-free conditions, catalytic amounts of sulfonic acids promote ester condensation between an equimolar mixture of carboxylic acids and alcohols. In particular, p-toluenesulfonic acid (TsOH) and 10-camphorsulfonic acid (CSA), which have appropriate acidities, efficiently catalyze the ester condensation of secondary alcohols without their decomposition. Since the present protocol does not require solvents under simple open-air conditions, a large amount of esters can be synthesized in a rather small apparatus.

Original languageEnglish
Pages (from-to)5017-5020
Number of pages4
JournalTetrahedron Letters
Volume49
Issue number34
DOIs
Publication statusPublished - Aug 18 2008
Externally publishedYes

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Sulfonic Acids
Condensation
Esters
Hygroscopic Agents
Alcohols
Esterification
Carboxylic Acids
Acidity
Decomposition

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Open-air and solvent-free ester condensation catalyzed by sulfonic acids. / Sakakura, Akira; Koshikari, Yoshiki; Ishihara, Kazuaki.

In: Tetrahedron Letters, Vol. 49, No. 34, 18.08.2008, p. 5017-5020.

Research output: Contribution to journalArticle

Sakakura, Akira ; Koshikari, Yoshiki ; Ishihara, Kazuaki. / Open-air and solvent-free ester condensation catalyzed by sulfonic acids. In: Tetrahedron Letters. 2008 ; Vol. 49, No. 34. pp. 5017-5020.
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