The Rosenmund reduction is a hydrogenation process in which an acyl chloride is selectively reduced to an aldehyde. The reaction was named after Karl Wilhelm Rosenmund, who first reported it in 1918.[1]
The reaction, a hydrogenolysis, is catalysed by palladium on barium sulfate, which is sometimes called the Rosenmund catalyst. Barium sulfate has a low surface area which reduces the activity of the palladium, preventing over-reduction. However, for certain reactive acyl chlorides the activity must be reduced further, by the addition of a poison. Originally this was thioquinanthrene although thiourea[2] has also been used.[3][4] Deactivation is required because the system must reduce the acyl chloride but not the subsequent aldehyde. If further reduction does take place, it will create a primary alcohol which would then react with the remaining acyl chloride to form an ester.
Rosenmund catalyst can be prepared by reduction of palladium(II) chloride solution in the presence of BaSO4. Typical reducing agent is formaldehyde.[5]
While Rosenmund reduction method can be used to prepare several aldehydes, formaldehyde cannot be prepared, as formyl chloride is unstable at room temperatures.[6]
^Rosenmund, K. W. (1918). "Über eine neue Methode zur Darstellung von Aldehyden. 1. Mitteilung". Chemische Berichte (in German). 51: 585–593. doi:10.1002/cber.19180510170.
^Weygand, Conrad; Meusel, Werner (12 May 1943). "Über die Abstimmung der katalytischen Hydrierung, III. Mitteil.: Thioharnstoff als Spezifikator bei der Bildung von Benzaldehyd aus Benzoylchlorid". Berichte der Deutschen Chemischen Gesellschaft (A and B Series) (in German). 76 (5): 503–504. doi:10.1002/cber.19430760510.
^Rosenmund, K. W.; Zetzsche, F. (1921). "Über die Beeinflussung der Wirksamkeit von Katalysatoren, 1. bis 5". Chemische Berichte (in German). 54 (3): 425–437, 638–647, 1092–1098, 2033–2037, 2038–2042. doi:10.1002/cber.19210540310.
^Mosettig, E.; Mozingo, R. (1948). "The Rosenmund Reduction of Acid Chlorides to Aldehydes". Organic Reactions. 4: 362–377. doi:10.1002/0471264180.or004.07. ISBN 0471264180.
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hydride donor, reduces acyl chlorides to aldehydes, as does the Rosenmundreduction using hydrogen gas over a poisoned palladium catalyst. With Lewis...
aldehyde through the Fukuyama reduction or Weinreb reaction respectively, or using catalytic hydrogenation as in the Rosenmund reaction. In the Weinreb ketone...
alkoxides. One of the key uses is to act as a catalyst poison in the Rosenmundreduction. It has the IUPAC name of 2,13-dithia-10,21-diazapentacyclo[12.8...
Halogenation with thionyl chloride gave CID:129921490 (7). Lastly, a Rosenmundreduction completed the total synthesis of mephentermine (8). According to...
and DIBAL, via the acid chloride in the Rosenmundreduction and via the thioester in the Fukuyama reduction. In ketonic decarboxylation carboxylic acids...
reaction that produces an aldehyde from an acyl halide. Because of the Rosenmundreduction and DIBAL-H accomplish similar transformations, this reaction sequence...
the reduction of palladium chloride in a slurry of calcium carbonate (CaCO3) followed by poisoning with lead acetate. In a related case, the Rosenmund reduction...
ISBN 9780387683508. Mosettig, Erich; Mozingo, Ralph (15 March 2011). "The RosenmundReduction of Acid Chlorides to Aldehydes". Organic Reactions: 362–377. doi:10...
achieved. Palladium on barium sulfate is also used as a catalyst in the Rosenmundreduction. As barium compounds emit a characteristic green light when heated...
Berlin for his work with Otto Diels. He discovered the Rosenmundreduction, which is the reduction of acid chlorides to aldehydes over palladium on barium...
or platinum. The Rosenmund route also uses hydrogen gas and a palladium catalyst poisoned with barium sulfate (Rosenmundreduction), but uses perchloric...
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its acid chloride, and then performing catalytic reduction on this compound using the Rosenmundreduction followed by deacetylation. The resultant product...
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reactions are: condensations, e.g., to prepare plasticizers and polyols, and reduction to produce alcohols, especially "oxo-alcohols". From the biological perspective...
mechanistically distinct pathways are known to cyanate arenes: While the classical Rosenmund Von-Braun reaction utilizes stoichiometric copper(I) cyanide as a cyanation...
Der Reiter Mir ist ein schöns brauns Maidelein Mein Mädel hat einen Rosenmund Ach, könnt ich diesen Abend Ich stand auf hohem Berge Es reit ein Herr...