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

Participants

Reaction Steps

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% Na2Cl3. 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.

Provenance & Evidence