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25.1.4.1 Reduction of Carboxylic Acid Chlorides

DOI: 10.1055/sos-SD-025-00031

Harcken, C.Science of Synthesis, (20072566.

The hydrogenolytic reduction of acid chlorides, the Rosenmund reduction, introduced in 1918, used to be the only reliable way to reduce a carboxylic acid derivative to an aldehyde.[‌3‌] The reaction is traditionally run with a poisoned palladium catalyst under harsh conditions, in refluxing toluene or xylene. Today the use of Rosenmund conditions has been replaced with the use of complex aluminum hydrides and borohydrides. The one notable advantage of reducing acid chlorides today, as with the reduction of thioesters, is the fact that conditions exist under which ketones are inert, a selectivity that cannot be accomplished with the use of any metal hydride reagent.

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