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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 21, 1991 - Issue 8-9
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Original Articles

The Birch Reduction - Dialkylation Reaction of Aromatic Carboxylic Acids. Identification of NaNH2 as the Base Responsible for the Second Alkylation

J. A. Guzmán División de Estudios de Posgrado, Facultad de Química, UNAM, 04512, México, D.F., México
,
R. Castanedo División de Estudios de Posgrado, Facultad de Química, UNAM, 04512, México, D.F., México
&
L. A. Maldonado División de Estudios de Posgrado, Facultad de Química, UNAM, 04512, México, D.F., México
Pages 1001-1012 | Received 22 Feb 1991, Published online: 23 Sep 2006
 
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Abstract

The Birch reduction-alkylation of 3,5-dimethoxybenzoic acid with excesses Na and EtBr gives 1,4-diethyl-3,5-dimethoxy-2, 5-cyclohexadiene carboxylic acid, 3. The responsible for the alkylation at C-4 has been identified as NaNH2, generated in Situ.

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