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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 1, 1971 - Issue 2
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Original Articles

A New Procedure for the Conversion of Cinnamaldehydes to Hydrocinnamaldehydes

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Pages 127-131 | Published online: 03 Jan 2007
 

Abstract

In connection with some of our reserch we were interested in preparing various substituted hydrocinnamaldhydes. The easiest approach seemed to be the reduction of the olefinic bond of the corresponding substituted cimamaldenyde. It was found that the selective reduction of aromatic α,β-unsaturated aldehydes present many difficulties because the olefinic bond and carbonyl groups are both easily reduced. The absorption of one equivalent of hydrogen by cinnamaldehyde can produce hydrocinnamaldehyde by the reduction of the olefinic bond, cinnamy1 alcohol by reduction of the carbony1 group,and hydrocinnamy1 alcohol by reduction of both the olefinic bond and carbony1 group. Various hydrogenolysis products can also be formed in lesser yields.

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