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

HRID 991037Notes

Reaction equation

HRID 991037 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 stired 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. temperaturerefluxed for 8 hrs
  2. customAt the end, reaction mixture
  3. filtrationwas filtered
  4. concentrationconcentrated
  5. customThe residue obtained
  6. extractionwas extracted with chloroform
  7. washwashed well with water
  8. customIt was dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-82cc8cd8350b432ab3f6529470e2b200
Source dataset
uspto-grants-2002_10
Patent number
US06462073B2

Reaction notes

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