Acrylic Acid → HCID 54279559, compound

HRID 1419077Notes

Reaction equation

HRID 1419077 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[C:9]([OH:13])(=[O:12])[CH:10]=[CH2:11]>CCOCC>[F:1][C:2]1[CH:3]=[C:4]([S:8][CH2:11][CH2:10][C:9]([OH:13])=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6581Acrylic AcidHCID 75710m-Fluorobenzenethiol

Product 1

HCID 54279559HCID 54279559, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-Fluorothiophenol (5.39 g, 42 mmol) was added to acrylic acid (3.73 g, 52 mmol) and stirred at room temperature for 20.2 hours. The reaction mixture solidified, was dissolved in ether and extracted with 10% Na2CO3. 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-fluorophenylthio)propanoic acid (6.75 g), contaminated with some acrylic acid, as a white solid which was used without further purification in the next step.

Workup

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

Sources & evidence

ORD record
ord-d0da6f43350d4eb69439608817f103e0
Source dataset
uspto-grants-1999_03
Patent number
US05886016

Reaction notes

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