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A novel synthesis of parent resorc[4]arene and its partial alkyl ethers |
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| Authors: | Jan Stursa Jan Smidrkal Jitka Moravcova |
| Institution: | a Department of Chemistry of Natural Compounds, Institute of Chemical Technology, Technicka 5, CZ-166 28 Prague 6, Czech Republic b Laboratory of NMR Spectroscopy, Institute of Chemical Technology, Technicka 5, CZ-166 28 Prague 6, Czech Republic c Department of Dairy Chemistry and Technology, Institute of Chemical Technology, Technicka 5, CZ-166 28 Prague 6, Czech Republic d Department of Solid State Chemistry, Institute of Chemical Technology, Technicka 5, CZ-166 28 Prague 6, Czech Republic |
| Abstract: | Treatment of 2,4-diisopropoxybenzyl alcohol with chlorotrimethylsilane in acetonitrile at room temperature for 1 h afforded a novel crystalline resorc4]arene octaisopropyl ether in 96% yield. Protecting groups were cleaved by boron trichloride in dichloromethane within 30 min and the parent resorc4]arene was isolated by flash chromatography in 76% yield. The outcome of the deprotection step was dependent on the conditions used as it is exemplified by a preparation of resorc4]arene heptaisopropyl ether. |
| Keywords: | Resorc[4]arene 2 4-Diisopropoxybenzyl alcohol Lewis acid Conformation Partially alkylated resorc[4]arene |
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