Safomuddin Abduahadi, Emmanuel Mintah Bonku, Hongjian Qin, Abdullajon Odilov, F. Zhu, H. Aisa, Jingshan Shen
{"title":"改进的碘催化芳香化反应及其在合成大麻二酚关键中间体中的应用","authors":"Safomuddin Abduahadi, Emmanuel Mintah Bonku, Hongjian Qin, Abdullajon Odilov, F. Zhu, H. Aisa, Jingshan Shen","doi":"10.1055/a-2301-2431","DOIUrl":null,"url":null,"abstract":"In this study, the development of an improved process for the synthesis of a key cannabidiol intermediate, methyl olivetolate, is described. The process involves an improvement of the iodine-catalyzed aromatization of cyclohexanone using potassium persulfate as an oxidant. This approach enabled for the efficient synthesis of methyl olivetolate with a 90% yield and 99.84% HPLC purity on a 5 kg scale. Additionally, a total of 16 cyclohexanone substrates afforded higher yields (75-92%) of m-diphenol compounds compared to the established methods.","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"20 6","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"An Improved Iodine-Catalyzed Aromatization Reaction and Its Application in the Synthesis of a Key Intermediate of Cannabidiol\",\"authors\":\"Safomuddin Abduahadi, Emmanuel Mintah Bonku, Hongjian Qin, Abdullajon Odilov, F. Zhu, H. Aisa, Jingshan Shen\",\"doi\":\"10.1055/a-2301-2431\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"In this study, the development of an improved process for the synthesis of a key cannabidiol intermediate, methyl olivetolate, is described. The process involves an improvement of the iodine-catalyzed aromatization of cyclohexanone using potassium persulfate as an oxidant. This approach enabled for the efficient synthesis of methyl olivetolate with a 90% yield and 99.84% HPLC purity on a 5 kg scale. Additionally, a total of 16 cyclohexanone substrates afforded higher yields (75-92%) of m-diphenol compounds compared to the established methods.\",\"PeriodicalId\":509029,\"journal\":{\"name\":\"Synlett\",\"volume\":\"20 6\",\"pages\":\"\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-04-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synlett\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1055/a-2301-2431\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synlett","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2301-2431","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
An Improved Iodine-Catalyzed Aromatization Reaction and Its Application in the Synthesis of a Key Intermediate of Cannabidiol
In this study, the development of an improved process for the synthesis of a key cannabidiol intermediate, methyl olivetolate, is described. The process involves an improvement of the iodine-catalyzed aromatization of cyclohexanone using potassium persulfate as an oxidant. This approach enabled for the efficient synthesis of methyl olivetolate with a 90% yield and 99.84% HPLC purity on a 5 kg scale. Additionally, a total of 16 cyclohexanone substrates afforded higher yields (75-92%) of m-diphenol compounds compared to the established methods.