Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 8, Pages 2536-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja9106989
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- Ministry of Education, Culture, Sports, Science and Technology, Japan
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Acetates were successfully alkylated with primary alcohols and alpha,omega-diols in the presence of tert-BuOK Under the influence of [IrCl(cod)](2). For instance, the reaction of tert-butyl acetate with eta-butanol in the presence of tert-BuOK as a base and [IrCl(cod)](2) as a catalyst in tert-BuOH at 100 degrees C produced tert-butyl hexanoate in good yield. When the alpha,omega-diol 1,9-nonanediol was employed, di-tert-butyl tridecanoate was obtained. These reaction,; are the first report of the alkylation of acetates Using alcohols as alkylating agents. This method provides a very convenient direct route to carboxylates, which are very important raw materials in organic and industrial chemistry.
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