Acrylic Acid → 3-(2,3-Dichlorophenylthio)propanoic acid

HRID 1419075Notes

Reaction equation

HRID 1419075 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[SH:9].[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12].C([O-])([O-])=O.[Na+].[Na+]>>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9][CH2:12][CH2:11][C:10]([OH:14])=[O:13]

Participants

4

Reactant 3

HCID 6581Acrylic AcidHCID 10340Sodium CarbonateHCID 1402022,3-Dichlorobenzenethiol

Product 1

HCID 218490133-(2,3-Dichlorophenylthio)propanoic acidYield 55.2%

Conditions

Temperature
50 °C

Procedure

2,3-Dichiorothiophenol (4.94 g, 28 mmol) was added to acrylic acid (2.11 g, 29 mmol) and stirred at 50° C. for 3 hours. The reaction mixture was poured into 10% Na2CO3 and extracted with ether. The aqueous layer was acidified with concentrated hydrochloric acid, extracted with ether, washed with brine, dried over MgSO4, and concentrated in vacuo to give the 3-(2,3-dichlorophenylthio)propanoic acid (3.88 g), contaminated with some acrylic acid, as a clear oil which was used without further purification in the next step.

Workup

  1. extractionextracted with ether
  2. extractionextracted with ether
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a7bc44455c3a48a7b88b5e56e940ae1a
Source dataset
uspto-grants-1999_03
Patent number
US05886016

Reaction notes

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