Acylation of 2-methoxynaphthalene over ion-exchanged ß-zeolite

Abstract

Friedel-Crafts acylation of 2-Methoxynaphthalene was carried out over various ion-exchanged β zeolites (Mn+β, where Mn+: In3+, Zn2+, Al3+, Fe3+, La3+) with various anhydride (acetic, propionic and benzoic anhydrides), or acyl chloride (acetyl, propionyl and benzoyl chlorides) acylating reagents. The results suggested that selectivity towards the 6-substituted products was higher with the larger size anhydrides, propionic and benzoic anhydrides. The metal cation type within the zeolite significantly influenced the extent of conversion and product distribution. That La3+ exchanged zeolite displayed higher selectivity for the 6-position acylated product with anhydrides ascribed mainly to narrowing of channels by the presence of La(OH)2+ ions that leave no room for the formation of more bulky isomeric forms and to enhanced Bronsted acidity of the zeolite. With acyl chlorides, the recovery of ketone products was found to be remarkably low. 1-Acyl-2-methoxynaphthalenes actively underwent deacylation when acyl chlorides were used as the acylation reagent.