{"title":"磷钨酸催化离子液体中2-甲氧基萘与乙酸酐的Friedel-Crafts酰化","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":"{\"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}","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
摘要
以磷钨酸(H3PW12O40)为催化剂,在离子液体(IL)四氟硼酸丁吡啶([BPy]BF4)中进行了2-甲氧基萘(2-MN)与乙酸酐(AA)的Friedel-Crafts酰化反应。[BPy] bf4介导的2-MN酰化反应对1-酰基-2-甲氧基萘(1-AC-2-MN)具有良好的转化率和选择性,在最优条件下,2-MN的转化率为70.4%,对1-AC-2-MN的选择性为96.4%。由于1- ac -2- mn的重排,反应1 h后可以检测到6-酰基-2-甲氧基萘(6-AC-2-MN),在该反应条件下,6-AC-2-MN的收率最高,为11.3%。该体系可循环使用至少6次,活性无明显损失,表明H3PW12O40/[BPy]BF4催化体系稳定性好。
Friedel-Crafts acylation of 2-methoxynaphthalene with acetic anhydride catalyzed by phosphotungstic acid in ionic liquid
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.