Zeolite catalysed synthesis of coumarin derivatives

✍ Scribed by Eric A. Gunnewegh; Anthonius J. Hoefnagel; Herman van Bekkum

• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 502 KB
• Volume: 100
• Category: Article
• ISSN: 1381-1169
• DOI: 10.1016/1381-1169(95)00156-5

✦ Synopsis

The direct synthesis of coumarin derivatives from m-substituted phenols and a&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 P-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.