Thionyl Chloride → 3-(2-Chloro-2-oxoethyl)phenyl acetate
Reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=O)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].S(Cl)([Cl:17])=O>>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([Cl:17])=[O:14])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]Participants
3
Procedure
A solution of 6.36 g 3-acetoxyphenylacetic acid and 10 ml of thionyl chloride was refluxed for one hour. The solvent was removed on a rotary evaporator, 15 ml of dry benzene was added and re-evaporated to yield crude 3-acetoxyphenylacetyl chloride. To a cooled solution of the acid chloride in 35 ml benzene was added dropwise a solution 8.9 g of octyl amine and 10 ml of ether. The reaction mixture was stirred at room temperature for three hours, the solids filtered, and the filtrate transferred to a separatory funnel and extracted with 50 ml of 1 N HCl, 50 ml of H2O and 50 ml of brine. The resulting organic solution was dried (MgSO4), filtered, and evaporated to yield 10.14 g of a mixture containing octyl 3-acetoxyphenylacetamide.
Workup
- customThe solvent was removed on a rotary evaporator, 15 ml of dry benzene