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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 9, 1979 - Issue 9
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Original Articles

Regiospecific Carboxylation of Certain Methoxylated 2-Tetralones

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Pages 819-824 | Received 04 Jun 1979, Published online: 05 Dec 2006
 

Abstract

As a part of an ongoing synthetic program, certain aromatic ringmethoxylated tetralins, bearing synthetically useful functional groups at positions 2 and 3, were required. The literature1 revealed that treatment of 6-methoxy-2-tetralone with NaH and dimethyl carbonate gave exclusive carbomethoylation at position 1. However, treatment of 2-tetralone and of 5-methoxy-2-tetralone with magnesium methoxy carbonate (“MMC”) followed by esterification with diazomethane was reported2 go give the 3-carbomethoxy product (la, lb) exclusively, although in low (12 and 26%, respectively) yield. The use of MMC in regiospecific carboxylation of certain acylic ketones has also been reported3.

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