Rosenmund reduction

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.

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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

• Grundmann aldehyde synthesis

References

1. ^ Rosenmund, K. W. (1918). "Über eine neue Methode zur Darstellung von Aldehyden. 1. Mitteilung". Chemische Berichte 51: 585 - 593. doi:10.1002/cber.19180510170.
2. ^ 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.
3. ^ 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.; 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:10.1002/prac.18730060111.