Thionyl Chloride → Fluorocinnamoyl chloride
Reaction equation
[F:1][C:2](=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3](O)=[O:4].S(Cl)([Cl:15])=O>ClCCl>[F:1][C:2](=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([Cl:15])=[O:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
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.
Workup
- dissolutionAfter the acid dissolved
- customThe solvent and unreacted thionylchloride were removed at a reduced pressure
- customfurther the solvent was completely removed at a high vacuum pressure
Sources & evidence
- ORD record
- ord-39229b38af1d449abe694f37fec05bee
- Source dataset
- uspto-grants-1999_12
- Patent number
- US05998101
Reaction notes
Loading…