Chloroacetone → Ethyl 2-(4-(2-oxopropylthio)phenyl)acetate

HRID 505586Notes

Reaction equation

HRID 505586 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][C:22](=[O:24])[CH3:23]>CC(C)=O.O>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:21][C:22](=[O:24])[CH3:23])=[CH:8][CH:7]=1)[CH3:2]

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 123300434-Mercapto-phenyl-acetic acid ethyl ester

Product 1

HCID 66764764Ethyl 2-(4-(2-oxopropylthio)phenyl)acetate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

To a solution of (4-mercaptophenyl)-acetic acid ethyl ester (10 g, 0.051 mol) in 150 mL of acetone is added potassium carbonate (anhydrous, 8.51 g, 0.061 mol) at 0° C., followed by dropwise addition of chloroacetone (5 mL, 0.061 mol) in 10 mL of acetone at 0° C. The reaction is then maintained at RT for 2 h. The reaction is filtered and the filtrate is concentrated under vacuum. The residue thus obtained is diluted with 15 mL of water and extracted with ethyl acetate (2×50 mL). The organic layer is then washed with water and brine, dried over sodium sulfate, filtered and evaporated under vacuum to give [4-(2-oxo-propylsulfanyl)-phenyl]-acetic acid ethyl ester as a yellow oil.

Workup

  1. filtrationThe reaction is filtered
  2. concentrationthe filtrate is concentrated under vacuum
  3. customThe residue thus obtained
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. washThe organic layer is then washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-2a94180bae4f40549d64e03ff205d57c
Source dataset
uspto-grants-2010_08
Patent number
US07781451B2

Reaction notes

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