Acrylic Acid → HCID 5314229, compound

HRID 865301Notes

Reaction equation

HRID 865301 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12]>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9][CH2:12][CH2:11][C:10]([OH:14])=[O:13])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6581Acrylic AcidHCID 849893-Methoxybenzenethiol

Product 1

HCID 5314229HCID 5314229, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-Methoxythiophenol (5.70 g, 41 mmol) was placed in a flask with acrylic acid (2.36 g, 33 mmol) and stirred at room temperature for 113.8 hours. The reaction mixture was dissolved in ether and extracted with 10% Na2CO3. The aqueous layer was acidified with concentrated HCl, extracted with ether, dried over MgSO4, and concentrated in vacuo to give the 3-(3-methoxyphenylthio)propanoic acid (2.55 g , 37%) as a white solid: mp 39°-42° C.; 1H NMR (CDCl3) 300 MHz 7.21 (m, 1H) 6.91 (m, 2H) 6.77 (d, J=8.3 Hz, 1H) 3.79 (s, 3H) 3.16 (t, J=7.5 Hz, 2H) 2.68 (t, J=7.3 Hz, 2H).

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-cf0360ca698a43fa8915837d9c7f0ad9
Source dataset
uspto-grants-1996_10
Patent number
US05565482

Reaction notes

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