The Rosenmund reduction is a chemical reaction that reduces an acid halide to an aldehyde using hydrogen gas over palladium-on-carbon poisoned with barium sulfate.[1][2][3] The reaction was named after Karl Wilhelm Rosenmund.
The catalyst must be poisoned because otherwise the catalyst is too active and will reduce the acid chloride to a primary alcohol.
Diisobutylaluminium hydride (DIBALH) can also reduce acid chlorides to aldehydes.
See also
References
- ^ Rosenmund, K. W. (1918). "Über eine neue Methode zur Darstellung von Aldehyden. 1. Mitteilung". Chemische Berichte 51: 585–593. doi:.
- ^ Rosenmund, K. W., Zetzsche, F. (1921). "Über die Beeinflussung der Wirksamkeit von Katalysatoren, 1. bis 5.". Chemische Berichte 54: 425–437; 638–647; 1092–1098; 2033–2037; 2038–2042.
- ^ Mosettig, E.; Mozingo, R. Org. React. 1948, 4, 362. (Review)
Further reading
- A. I. Rachlin, H. Gurien, and D. P. Wagner (1988), "Aldehydes from Acid Chlorides by modified Rosenmund Reduction: 3,4,5-Trimethoxybenzaldehyde", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p1007; Coll. Vol. 6: 1007
- Saytzeff, M. (1873). "Ueber die Einwirkung des vom Palladium absorbirten Wasserstoffes auf einige organische Verbindungen". Journal für Praktische Chemie 6 (1): 128–135. doi:.
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