Zeolite catalysed synthesis of coumarin derivatives

• Published in: Journal of molecular catalysis. A, Chemical Vol. 100; no. 1; pp. 87 - 92
• Main Authors: Gunnewegh, Eric A., Hoefnagel, Anthonius J., van Bekkum, Herman
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 23.11.1995; Elsevier
• Subjects: 3-substituted phenol; Catalysis; Catalytic reactions; Chemistry; Coumarin synthesis; Exact sciences and technology; General and physical chemistry; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Zeolite H-Beta; α,β-unsaturated carboxylic acid; Zeolite H-Beta; α,β-unsaturated carboxylic acid; Coumarin synthesis; 3-substituted phenol; Catalytic reaction; Aliphatic compound; Acrylic acid; Coumarine derivatives; Zeolite; Experimental study; Alkylation; Esterification; Molecular sieve; Resorcinol; Heterogeneous catalysis; Synthesis; Carboxylic acid; Reaction mechanism; Phenols; Benzenic compound; Catalyst; Ethylenic compound
• ISSN: 1381-1169; 1873-314X
• DOI: 10.1016/1381-1169(95)00156-5

The direct synthesis of coumarin derivatives from m-substituted phenols and α,β-unsaturated carboxylic acids catalysed by solid-acid catalysts, such as zeolite H-Beta or Amberlyst-15, in toluene as solvent was studied. The conversion involves esterification followed by alkylation (ring closure). Ring closure of the ester is promoted both by an appropriate substituent on the aromatic ring and by Michael activation of the β-carbon of the ester. These influences were studied by variation of the reactants. 7-Hydroxy-3,4-dihydrocoumarin is formed in high yield when resorcinol and propenoic acid are used as reactants.