Reaction #631971

ord-43b48e2ce5cd45609b530a2602e1348d

Reaction equation

C=CC(=O)OCCC(=O)O
2-Carboxyethyl acrylate
O=S(Cl)Cl
Thionyl chloride
→
C=CC(=O)OCCC(=O)Cl
desired product
C=CC(=O)OCCC(=O)Cl
3-chloro-3-oxopropyl acrylate

Reactants

C=CC(=O)OCCC(=O)O
2-Carboxyethyl acrylate
O=S(Cl)Cl
Thionyl chloride

Reagents

None

Solvents

ClCCl
CH2Cl2

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturethe solution is cooled in an ice bath
  2. 2
    OtherThe solvent is removed under reduced pressure

Procedure

2-Carboxyethyl acrylate (1 eq.) is dissolved in CH2Cl2 and the solution is cooled in an ice bath. Thionyl chloride (1 eq.) is added dropwise and the mixture is allowed to warm to room temperature and stir for 4 hours. The solvent is removed under reduced pressure and the desired product is isolated by vacuum distillation.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07935131B2uspto-grants-2011_05