Sulfur Dioxide → HCID 13497266, compound

Participants

Reaction Steps

To a solution of 69.6 g of 2-cyano-3-hydroxy-4,4-dimethyl- 2-pentenenitrile in 600 ml of methylene chloride was added in small portions 104.1 g of phosphorus pentachloride. The mixture was stirred for 22 hours at room temperature. Sulfur dioxide was passed through the mixture for 20 minutes and the mixture stirred for an additional hour. The mixture was concentrated and poured into 500 ml of ice. After stirring for 1 hour, the cold mixture was filtered, the solid was washed with cold water and dried in a vacuum oven at room temperature for 60 hours to give 68.8 g of 3-chloro-2-cyano-4,4-dimethyl- 2-pentenenitrile, mp 52°-53°.

Provenance & Evidence