Acetone → Ethyl 2-[(4-ethoxyphenyl)sulfanyl]propanoate

HRID 1595573Notes

Reaction equation

HRID 1595573 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([S:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[CH3:6])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH3:22][C:23](C)=O>>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([S:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:22][CH3:23])=[CH:12][CH:13]=1)[CH3:6])[CH3:2]

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 109771882-[(4-Hydroxyphenyl)thio]propanoic acid ehtyl ester

Product 1

HCID 10934051Ethyl 2-[(4-ethoxyphenyl)sulfanyl]propanoate

Procedure

To stirred solution of 2-(4-hydroxy-phenylsulfanyl)-propionic acid ethyl ester (11.3 g, 50 mmol), and K2CO3 (50 g, excess) in acetone (300 ml) ethyl iodide (20 ml, excess) was added and refluxed for 8 hrs. At the end, reaction mixture was filtered and concentrated. The residue obtained was extracted with chloroform and washed well with water. It was dried and concentrated. The product, 2-(4-ethoxy-phenylsulfanyl)-propionic acid ethyl ester was isolated as colorless oil. Yield: 12.0 g, 98%; MS: 255 (M+H).

Workup

  1. additionwas added
  2. temperaturerefluxed for 8 hrs
  3. customAt the end, reaction mixture
  4. filtrationwas filtered
  5. concentrationconcentrated
  6. customThe residue obtained
  7. extractionwas extracted with chloroform
  8. washwashed well with water
  9. customIt was dried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-5823247ed9af4ad2a11c8380631c2576
Source dataset
uspto-grants-2001_09
Patent number
US06288086B1

Reaction notes

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