{"title":"Friedel-Crafts acylation of 2-methoxynaphthalene with acetic anhydride catalyzed by phosphotungstic acid in ionic liquid","authors":"Y. Guo, J. Sun, F. Guo, Yu He, P. Chen","doi":"10.34049/BCC.51.2.4449","DOIUrl":null,"url":null,"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.","PeriodicalId":9289,"journal":{"name":"Bulgarian Chemical Communications","volume":"1 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Bulgarian Chemical Communications","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.34049/BCC.51.2.4449","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"Chemistry","Score":null,"Total":0}
引用次数: 0
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.