Article
2022
·
8 citations
Deoxygenative Chlorination of Aldehydes and Alcohols with Dichloromethyl Methyl Ether and TiCl<sub>4</sub>
Abstract
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.
Keywords
Benzal chlorides
Deoxy-chlorination
Double formylation
Geminal dichlorides
Rieche formylation
UBER ALPHA-HALOGENATHER
MEDICINAL CHEMISTRY
BENZAL HALIDES
FORMYLATION
EFFICIENT
DICHLORIDES
OLEFINATION
CONVERSION
SCOPE
WoS Categories
Chemistry, Organic
Citation
- Journal
- EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
- Year
- 2022
- Volume
- 2022
- Issue
- 45
- ISSN
- 1434-193X
- eISSN
- 1099-0690
- DOI
- 10.1002/ejoc.202201106
- WoS UID
- WOS:000894491600010