Rosenmund reduction

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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 Rosenmund reduction

The reaction is catalysed by palladium on barium sulphate, however its activity must often be regulated by the addition of a poison; normally thioquinanthrene although thiourea[2] has also been used.[3][4] This is required because the system must reduce the acyl choride but not the subsequent aldehyde. If further reduction does take place then the resulting primary alcohol will react with the remaining acyl chloride to form an ester.

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References[edit]

  1. ^ 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. 
  2. ^ 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. 
  3. ^ 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. 
  4. ^ Mosettig, E.; Mozingo, R. (1948). "The Rosenmund Reduction of Acid Chlorides to Aldehydes". Organic Reactions 4: 362–377. doi:10.1002/0471264180.or004.07. 

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