HYDROCHLORINATION OF 2,3-ACETYLENIC ACIDS WITH THIONYL CHLORIDE IN DIMETHYLFORMAMIDE

ABSTRACT

The reaction of 2,3-acetylenic acids (1a–d) with thionyl chloride in DMF under mild conditions gave E,Z-3-chloro-2-alkenoic acids (2a–d) or esters (3a–d) depending on treating the reaction mixture with either water or alcohols.

Keywords:

• Hydrochlorination
• Acetylenic acids
• 3-Chloro-2-propenoic acids
• Thionyl chloride
• Dimethylformamide

ACKNOWLEDGMENTS

The authors would like to thank NMR Laboratory at Chemistry Department-Universidad Simón Bolívar (Proyect BID-CONICIT QF-13) and The National NMR Laboratory.