Acrylic Acid → 3-[(3-Chlorophenyl)sulfanyl]propanoic acid

HRID 1078332Notes

Reaction equation

HRID 1078332 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[Cl:6][C:7]1[CH:8]=[C:9]([SH:13])[CH:10]=[CH:11][CH:12]=1>CCOCC>[Cl:6][C:7]1[CH:8]=[C:9]([S:13][CH2:3][CH2:2][C:1]([OH:5])=[O:4])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 6581Acrylic AcidHCID 162573-Chlorothiophenol

Product 1

HCID 242791353-[(3-Chlorophenyl)sulfanyl]propanoic acidYield 34%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Acrylic acid (2.66 g, 37 mmol) and 3-chlorothiophenol (4.85 g, 34 mmol) were dissolved in ether (15 mL) and stirred at room temperature for 88.0 hours. The reaction mixture solidified, was dissolved in ether and extracted with 5% NaOH. 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-(3-chlorophenylthio)propanoic acid (2.20 g, 34%): 1H NMR (acetone-d6) 300 MHz 7.33-7.40 (m, 3H) 7.24 (m, 1H) 3.25 (t, J=7.1 Hz, 2H) 2.67 (t, J=7.1 Hz, 2H). Mass spectrum: M+H=217.

Workup

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

Sources & evidence

ORD record
ord-f777fbc6a8654dd1a722364978cf6a6f
Source dataset
uspto-grants-1996_08
Patent number
US05547975

Reaction notes

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