The effect of various phenolics in p-tsoh-catalyzed solvent-free microwave-assisted synthesis of 4-methyl coumarin derivatives

H. Dianhar, A. W. Winata, S. Handayani, P. Sugita, D. U.C. Rahayu

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Coumarin derivatives from natural and synthetic sources are an important class of heterocyclic compounds that displayed a broad spectrum of pharmacological properties. Among all coumarin derivatives, 4-methyl coumarin has been essentially used as a building block to afford various chemical structures. In this study, the effect of various phenolics and catalytic activity of p-TsOH for synthesizing 4-methyl coumarin derivatives has been investigated under conventional heating and microwave conditions. The highest yield of 4-methyl coumarin derivatives synthesis was achieved using resorcinol (60.10 + 2.9% yield) in the optimum reaction condition of starting materials molar ratio (1:1, resorcinol/ethyl acetoacetate, mol/mol) and 10 mol% of p-TsOH using 800W microwave irradiation at 80o C for 180s under solvent-free condition. Microwave-assisted condition revealed a useful and simple method to synthesize coumarin derivatives through Pechmann condensation under neat and mild conditions with moderate to high yield, short reaction time, and easier product work-up using organic Brønsted acid catalyst.

Original languageEnglish
Pages (from-to)1801-1806
Number of pages6
JournalRasayan Journal of Chemistry
Volume13
Issue number3
DOIs
Publication statusPublished - 1 Jul 2020

Keywords

  • 4-Methyl Coumarin
  • Microwave-assisted
  • p-TsOH Catalyst
  • Pechmann Condensation
  • Phenolics
  • Solvent-free

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