Thionyl Chloride → 3-Chloro-3-oxopropyl acrylate

HRID 1920598Notes

Reaction equation

HRID 1920598 reaction equation
[C:1]([O:5][CH2:6][CH2:7][C:8]([OH:10])=O)(=[O:4])[CH:2]=[CH2:3].S(Cl)([Cl:13])=O>C(Cl)Cl>[C:1]([O:5][CH2:6][CH2:7][C:8]([Cl:13])=[O:10])(=[O:4])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 905582-Carboxyethyl acrylate

Product 1

HCID 574289913-Chloro-3-oxopropyl acrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. temperaturethe solution is cooled in an ice bath
  2. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-3f3abedbb19f4df180d7ce0333dcec44
Source dataset
uspto-grants-2012_05
Patent number
US08172873B2

Reaction notes

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