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The synthesis of aldehydes by means of a modified Rosenmund reduction of acid chlorides

✍ Scribed by J. A. Peters; H. van Bekkum

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
428 KB
Volume
100
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

Aliphatic as well as aromatic acid chlorides are reduced smoothly into aldehydes at room temperature and atmospheric pressure by hydrogenation, using palladium on carbon as the catalyst, acetone or ethyl acetate as solvent and ethyldiisopropylamine as hydrogen chloride acceptor. The reaction has a high selectivity and under the conditions used, no over‐reduction nor reduction of aromatic rings, of nitro and chloro substituents in benzoyl chlorides, or double bonds in cinnamoyl chlorides, was observed. The selectivity is probably the result of a combination of factors, such as selective adsorption of the acid chloride on the catalyst (with respect to the aldehyde) and partial poisoning of the catalyst surface by co‐adsorption of ethyldiisopropylamine and its hydrochloride.

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