Carboxylation of hydroxyarens with metal alkyl carbonates
The objective of this work was to investigate the possibility of using alkali metal salts of ethylcarbonic acid as a carboxylating reagent in phenol (naphthols) carboxylation and developing a new and simple method for the synthesis of hydroxybenzoic and hydroxynaphthoic acids having broad practical...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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De Gruyter
2015-04-01
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| Series: | Green Processing and Synthesis |
| Subjects: | |
| Online Access: | https://doi.org/10.1515/gps-2014-0098 |
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| author | Suerbaev Khakim A. Aldabergenov Mayliby K. Kudaibergenov Nurbolat Zh. |
| author_facet | Suerbaev Khakim A. Aldabergenov Mayliby K. Kudaibergenov Nurbolat Zh. |
| author_sort | Suerbaev Khakim A. |
| collection | DOAJ |
| description | The objective of this work was to investigate the possibility of using alkali metal salts of ethylcarbonic acid as a carboxylating reagent in phenol (naphthols) carboxylation and developing a new and simple method for the synthesis of hydroxybenzoic and hydroxynaphthoic acids having broad practical application. It was found that sodium ethyl carbonate and potassium ethyl carbonate can be successfully used as carboxylating agents in carboxylation of phenol and naphthols. For the first time, the effects of the gaseous medium (air, carbon dioxide, argon), pressure, temperature and reaction time on the proceedings of the carboxylation reactions were examined. Simple and convenient procedures for the syntheses of o- and p-hydroxybenzoic, p-aminosalicylic, 1-hydroxy-2-naphthoic, 1-hydroxy-4-naphthoic and 2-hydroxy-3-naphthoic acids were developed. New efficient technologies for preparation of drugs salicylic acid (antiseptic activity), p-aminosalicylic acid (antituberculous activity) and p-hydroxybenzoic acid (bactericide activity) based on carboxylation reactions of phenol and m-aminophenol with sodium and potassium salts of ethyl carbonic acid were worked out. |
| first_indexed | 2024-12-22T07:21:12Z |
| format | Article |
| id | doaj.art-484958daa672426dbb65b1d92c6ddb84 |
| institution | Directory Open Access Journal |
| issn | 2191-9542 2191-9550 |
| language | English |
| last_indexed | 2024-12-22T07:21:12Z |
| publishDate | 2015-04-01 |
| publisher | De Gruyter |
| record_format | Article |
| series | Green Processing and Synthesis |
| spelling | doaj.art-484958daa672426dbb65b1d92c6ddb842022-12-21T18:34:15ZengDe GruyterGreen Processing and Synthesis2191-95422191-95502015-04-0142919610.1515/gps-2014-0098Carboxylation of hydroxyarens with metal alkyl carbonatesSuerbaev Khakim A.0Aldabergenov Mayliby K.1Kudaibergenov Nurbolat Zh.2Faculty of Chemical Technology and Chemistry, Al-Faraby Kazakh National University, Al-Farabi av, 71 Almaty 050038, Republic of KazakhstanFaculty of Chemical Technology and Chemistry, Al-Faraby Kazakh National University, Al-Farabi av, 71 Almaty 050038, Republic of KazakhstanFaculty of Chemical Technology and Chemistry, Al-Faraby Kazakh National University, Al-Farabi av, 71 Almaty 050038, Republic of KazakhstanThe objective of this work was to investigate the possibility of using alkali metal salts of ethylcarbonic acid as a carboxylating reagent in phenol (naphthols) carboxylation and developing a new and simple method for the synthesis of hydroxybenzoic and hydroxynaphthoic acids having broad practical application. It was found that sodium ethyl carbonate and potassium ethyl carbonate can be successfully used as carboxylating agents in carboxylation of phenol and naphthols. For the first time, the effects of the gaseous medium (air, carbon dioxide, argon), pressure, temperature and reaction time on the proceedings of the carboxylation reactions were examined. Simple and convenient procedures for the syntheses of o- and p-hydroxybenzoic, p-aminosalicylic, 1-hydroxy-2-naphthoic, 1-hydroxy-4-naphthoic and 2-hydroxy-3-naphthoic acids were developed. New efficient technologies for preparation of drugs salicylic acid (antiseptic activity), p-aminosalicylic acid (antituberculous activity) and p-hydroxybenzoic acid (bactericide activity) based on carboxylation reactions of phenol and m-aminophenol with sodium and potassium salts of ethyl carbonic acid were worked out.https://doi.org/10.1515/gps-2014-0098carboxylationhydroxybenzoic acidshydroxynaphthoic acidsnaphtholsphenol |
| spellingShingle | Suerbaev Khakim A. Aldabergenov Mayliby K. Kudaibergenov Nurbolat Zh. Carboxylation of hydroxyarens with metal alkyl carbonates Green Processing and Synthesis carboxylation hydroxybenzoic acids hydroxynaphthoic acids naphthols phenol |
| title | Carboxylation of hydroxyarens with metal alkyl carbonates |
| title_full | Carboxylation of hydroxyarens with metal alkyl carbonates |
| title_fullStr | Carboxylation of hydroxyarens with metal alkyl carbonates |
| title_full_unstemmed | Carboxylation of hydroxyarens with metal alkyl carbonates |
| title_short | Carboxylation of hydroxyarens with metal alkyl carbonates |
| title_sort | carboxylation of hydroxyarens with metal alkyl carbonates |
| topic | carboxylation hydroxybenzoic acids hydroxynaphthoic acids naphthols phenol |
| url | https://doi.org/10.1515/gps-2014-0098 |
| work_keys_str_mv | AT suerbaevkhakima carboxylationofhydroxyarenswithmetalalkylcarbonates AT aldabergenovmaylibyk carboxylationofhydroxyarenswithmetalalkylcarbonates AT kudaibergenovnurbolatzh carboxylationofhydroxyarenswithmetalalkylcarbonates |