Acrylic Acid → HCID 54279559, compound

HRID 865296Notes

Reaction equation

HRID 865296 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 placed in a flask with 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-d4cbbcf694234bbf85fbab96db9f5c62
Source dataset
uspto-grants-1996_10
Patent number
US05565482

Reaction notes

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