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

HRID 1379132Notes

Reaction equation

HRID 1379132 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]>>[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

3

Reactant 2

HCID 6581Acrylic AcidHCID 1402022,3-Dichlorobenzenethiol

Product 1

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

Conditions

Temperature
50 °C

Procedure

2,3-Dichlorothiophenol (4.94 g, 28 mmol) was placed in a flask with acrylic acid (2.11 g, 29 mmol) and stirred at 50° C. for 3 hours. The reaction mixture was poured into 10% Na2Cl3 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-8a1dc912a55a46fc8250c0c1b14ab645
Source dataset
uspto-grants-1997_09
Patent number
US05670532

Reaction notes

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