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

HRID 2305844Notes

Reaction equation

HRID 2305844 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 The residue
  6. customobtained
  7. extractionwas extracted with chloroform
  8. washwashed well with water
  9. customIt was dried

Sources & evidence

ORD record
ord-1e76b96203e84a31b1006861a6b65d5a
Source dataset
uspto-grants-2002_08
Patent number
US06441023B1

Reaction notes

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