Published January 1, 2022
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Deoxygenative Chlorination of Aldehydes and Alcohols with Dichloromethyl Methyl Ether and TiCl4
Description
Here, we report highly efficient deoxygenative chlorination of aldehydes and alcohols with a dichloromethyl methyl ether and TiCl4 system. The method converts various aldehydes and alcohols into the desired geminal dichlorides or chlorides with good to excellent yields (up to 99 %). Combined with a subsequent Rieche formylation step using the same reagent system, this method provides an efficient approach for synthesis of aromatic dialdehydes. This strategy involves deoxy-chlorination of the aryl aldehydes followed by a second formylation of more activated benzal chloride derivatives. Dialdehydes can be easily obtained by hydrolyzing the corresponding of dichloromethyl derivative.
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