Friedel-Crafts acylation of 2-methoxynaphthalene with acetic anhydride catalyzed by phosphotungstic acid in ionic liquid-Reference-Cited by-同舟云学术

Friedel-Crafts acylation of 2-methoxynaphthalene with acetic anhydride catalyzed by phosphotungstic acid in ionic liquid

Published:2019 Issue:2 Volume:51 Page:289-295
ISSN:0324-1130
Container-title:Bulgarian Chemical Communications
language:en
Short-container-title:BCC

Author:

Guo Y.¹,Sun J.¹,Guo F.¹,He Yu.¹,Chen P.¹

Affiliation:

1. School of Chemistry and Materials Science, Liaoning Shihua University, Fushun 113001, China

Abstract

The Friedel-Crafts acylation of 2-methoxynaphthalene (2-MN) with acetic anhydride (AA) was carried out in the ionic liquid (IL) butylpyridinium tetrafluoroborate ([BPy]BF4) using phosphotungstic acid (H3PW12O40) as the catalyst. The [BPy]BF4-mediated 2-MN acylation displays good conversion and selectivity towards 1-acyl-2-methoxynaphthalene (1-AC-2-MN), with 70.4% conversion of 2-MN and 96.4% selectivity to 1-AC-2-MN obtained under the optimal conditions. Owing to the rearrangement of 1-AC-2-MN, 6-acyl-2-methoxynaphthalene (6-AC-2-MN) can be detected after 1 h of reaction time, with the highest 6-AC-2-MN yield of 11.3% obtained under the examined reaction conditions. The system can be recycled and reused at least 6 times without significant loss of activity, indicating the good stability of the H3PW12O40/[BPy]BF4 catalytic system.

Publisher

Institute of Chemical Engineering, Bulgarian Academy of Sciences

Subject

General Chemistry

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