Acrylic Acid → 3-[(3,4-Dimethoxyphenyl)sulfanyl]propanoic acid

HRID 1419080Notes

Reaction equation

HRID 1419080 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:12]([OH:16])(=[O:15])[CH:13]=[CH2:14]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][CH2:14][CH2:13][C:12]([OH:16])=[O:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 6581Acrylic AcidHCID 1365393,4-Dimethoxybenzene-1-thiol

Product 1

HCID 187901843-[(3,4-Dimethoxyphenyl)sulfanyl]propanoic acidYield 76.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3,4-Dimethoxythiophenol (5.00 g, 29 mmol) was placed in a flask with acrylic acid (2.27 g, 32 mmol) and stirred at room temperature for 22.4 hours. The reaction mixture solidified, was dissolved in ethyl acetate and extracted with 10% Na2CO3. The aqueous layer was acidified with concentrated hydrochloric acid, extracted with ether, dried over MgSO4, and concentrated in vacuo to give 3-(3,4-dimethoxyphenylthio)propanoic acid (5.39 g , 76%), contaminated with some acrylic acid, as a white solid which was used without further purification in the next step: mp 62°-64° C.; 1H NMR (CDCl3) 300 MHz 9.80 (br s, 1H) 7.01 (d, J=8.3 Hz, 1H) 6.98 (s, 1H) 6.82 (d, J=8.3 Hz, 1H) 3.87 (s, 3H) 3.86 (s, 3H) 3.06 (t, J=7.3 Hz, 2H) 2.63 (t, J=7.3 Hz, 2H). Mass spectrum: M+=242.

Workup

  1. extractionextracted with 10% Na2CO3
  2. extractionextracted with ether
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87dd56aeb06c46ca88fbca0bc56c89d8
Source dataset
uspto-grants-1999_03
Patent number
US05886016

Reaction notes

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