Acrylic Acid → HCID 53831006, compound

HRID 1078326Notes

Reaction equation

HRID 1078326 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[SH:10])([CH3:3])[CH3:2].[C:11]([OH:15])(=[O:14])[CH:12]=[CH2:13]>C(OCC)(=O)C>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:13][CH2:12][C:11]([OH:15])=[O:14])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6581Acrylic AcidHCID 96003Benzenethiol, 2-(1-methylethyl)-

Product 1

HCID 53831006HCID 53831006, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Isopropylthiophenol (4.77 g, 31 mmol) was placed in a flask with acrylic acid (2.37 g, 33 mmol) and stirred at room temperature for 71.8 hours. The reaction mixture solidified, was dissolved in ethyl acetate and extracted with 5% NaOH. The aqueous layer was acidified with concentrated hydrochloric acid, extracted with ethyl acetate, dried over MgSO4, and concentrated in vacuo to give 3-(2-isopropylphenylthio)propanoic acid (6.85 g), contaminated with some acrylic acid, as a yellow solid which was used without further purification in the next step.

Workup

  1. extractionextracted with 5% NaOH
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8811669e3a94308839eb956ad6e9e60
Source dataset
uspto-grants-1996_08
Patent number
US05547975

Reaction notes

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