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

HRID 1531035Notes

Reaction equation

HRID 1531035 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 concentrared. 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

Sources & evidence

ORD record
ord-71163246dd2a4973bf417e158321060d
Source dataset
uspto-grants-2001_03
Patent number
US06197791B1

Reaction notes

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