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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 12
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Original Articles

A Convenient Synthesis of 2-Alkyl-mono-O-alkylated and 2-Alkyl Resorcinols

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Pages 1869-1876 | Received 09 Apr 1990, Published online: 24 Oct 2006
 

Abstract

The title C, O -dialkylated resorcinols have seldom been prepared. We have developed a practical synthesis of this class of compounds starting with cyclohexane-1,3-dione. The key features of the synthesis are mono-O-alkylation of a 2-alkyl cyclohexane-1,3-dione and Pd-C catalyzed or NBS/DBU annuitization of the resultant O-alkyl-2-alkyl cyclohexane-1,3-dione. The use of cyclohexane-1,3-dione allows regioselective alkylations that would not be possible with resorcinol itself. A convenient synthesis of 2-alkyl resorcinols from cyclohexane-1,3-dione has also been achieved.

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