Alkylierung von Polyphenolderivaten, III. 2,6-Di-n-alkyl-1,4-benzochinone mit langen Alkylketten

作者: Gottfried Schill , Clemens Zürcher , Enno Logemann

DOI: 10.1002/CBER.19751080526

关键词:

摘要: Es wird die Synthese der 2,6-Dodecyl-1,4-benzochinone 7, 13 und 23 beschrieben. Die Einfuhrung Dodecylreste erfolgte durch Acylierung entsprechender Phenolather mit Dodecansaure/Bortrifluorid und/oder Metallierung anschliesender Alkylierung 1-Bromdodecan. dialkylierten 5, 11 20 wurden Bortribromid entmethyliert Salpetersaure bzw. Eisen(III)-sulfat zu den Chinonen dehydriert. Alkylation of Polyphenol Derivatives, III. 2,6-Di-n-alkyl-1,4-benzoquinones with Long Alkyl Chains The syntheses 1,4-benzoquinones 13, and 23, substituted in the 2,6-positions dodecyl residues, are described. The corresponding phenol ethers were acylated dodecanoic acid/boron trifluoride and/or metalated then alkylated 1-bromododecane. dialkylated 11, demethylated boron tribromide dehydrogenated to benzoquinones nitric acid or iron(III) sulfate, respectively.

参考文章(23)
Alexander T. Shulgin, The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). Journal of Medicinal Chemistry. ,vol. 9, pp. 445- 446 ,(1966) , 10.1021/JM00321A058
Walter Vetter, Gottfried Schill, Clemens Zürcher, Thermolyse von Acetoxy-alkylbenzolen und Hydroxy- alkylbenzolen Chemische Berichte. ,vol. 107, pp. 424- 441 ,(1974) , 10.1002/CBER.19741070207
Gottfried Schill, Enno Logemann, Clemens Zürcher, Aliphatic 1,2,3‐Triketones by Ozonolysis of Dialkyl‐1,4‐benzoquinones Angewandte Chemie. ,vol. 11, pp. 1089- 1089 ,(1972) , 10.1002/ANIE.197210891
Gottfried Schill, Enno Logemann, Clemens Zürcher, Aliphatische 1,2,3‐Triketone durch Ozonolyse von Dialkyl‐1,4‐benzochinonen Angewandte Chemie. ,vol. 84, pp. 1144- 1144 ,(1972) , 10.1002/ANGE.19720842305
F. M. Stoyanovich, B. P. Fedorov, Synthesis of 2-Alkyl-1,3-dilithiobenzenes and 2-Alkylisophthalic Acids Angewandte Chemie International Edition in English. ,vol. 5, pp. 127- 127 ,(1966) , 10.1002/ANIE.196601271
J.F.W. McOmie, M.L. Watts, D.E. West, Demethylation of aryl methyl ethers by boron tribromide Tetrahedron. ,vol. 24, pp. 2289- 2292 ,(1968) , 10.1016/0040-4020(68)88130-X
Henry Gilman, Frank K. Cartledge, The analysis of organolithium compounds Journal of Organometallic Chemistry. ,vol. 2, pp. 447- 454 ,(1964) , 10.1016/S0022-328X(00)83259-3