Thionyl Chloride → Fluorocinnamoyl chloride

Participants

Reaction Conditions

Reaction Steps

Fluorocinnamic acid (10 g, 0.06 mole) was dissolved in dichloromethane, and 8.59 g (0.07 mole) of thionylchloride was added dropwise to the solution. After the acid dissolved and the solution appeared clear, the reaction mixture was maintained at about 50° C. for 1 hour. The solvent and unreacted thionylchloride were removed at a reduced pressure and further the solvent was completely removed at a high vacuum pressure to give fluorocinnamoyl chloride. The fluorocinnamoyl chloride was dissolved in dried dichloromethane. A mixture of polyhydroxystyrene having a molecular weight of 22,000 and 6.07 g (0.06 mole) of triethylamine was dissolved in dichloromethane and a small amount of tetrahydrofuran. To this solution, the fluorocinnamoyl chloride solution was added dropwise while the temperature was maintained at 0° C. After keeping for 1 day, the resulting solution was washed with water to remove the solvent and amine salt. Polyhydroxystyrenylfluorocinnamate was obtained.

Provenance & Evidence