Grundmann aldehyde synthesis

What is Grundmann aldehyde synthesis?

The Grundmann aldehyde synthesis involves converting an acid chloride to an acetoxy ketone via a diazo ketone intermediate. This acetoxy ketone is then reduced using aluminum isopropoxide, hydrolyzed to glycol, and finally cleaved with lead tetraacetate to yield an aldehyde of the same chain length as the original acid.

Grundmann aldehydes synthesis
Grundmann aldehyde synthesis

References

Grundmann, C. (1936), Ein neues Verfahren zur Überführung von Carbonsäuren in Aldehyde. [A new process for the conversion of carboxylic acids into aldehydes] Justus Liebigs Ann. Chem., 524: 31-48. https://doi.org/10.1002/jlac.19365240105

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