Potassium Iodide → Methyl 2-(4-chlorobenzylthio)acetate

HRID 2285930Notes

Reaction equation

HRID 2285930 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][SH:13])=[CH:10][CH:9]=1.Cl[CH2:17][C:18]([O:20][CH3:21])=[O:19].[I-].[K+]>CC(C)=O>[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][S:13][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 804094-Chlorobenzyl mercaptan

Product 1

HCID 3311340Methyl 2-(4-chlorobenzylthio)acetateYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Anhydrous acetone (100 ml), potassium carbonate (21 g), p-chlorobenzylmercaptan (19.5 ml), methyl chloroacetate (13.2 ml) and potassium iodide (0.1 g) are mixed whilst cold. The mixture which is thus obtained is stirred and heated under reflux for 7 hours. It is then cooled, the precipitate (K2CO3) is filtered off, the acetone is evaporated from the filtrate and the residue is taken up in ether. The ether solution is washed with 4 N NaOH and then with water until the wash waters have a neutral pH. It is then dried over MgSO4, the ether is evaporated off and 34.5 g (yield 100%) of methyl 2-(4-chlorobenzylmercapto)-acetate are collected in the form of a chromatographically pure oil.

Workup

  1. customThe mixture which is thus obtained
  2. temperatureheated
  3. temperatureunder reflux for 7 hours
  4. temperatureIt is then cooled
  5. filtrationthe precipitate (K2CO3) is filtered off
  6. customthe acetone is evaporated from the filtrate
  7. washThe ether solution is washed with 4 N NaOH
  8. dry with materialIt is then dried over MgSO4
  9. customthe ether is evaporated off

Sources & evidence

ORD record
ord-039e24d6118249ae80960624ca0d840d
Source dataset
uspto-grants-1982_04
Patent number
US04325964

Reaction notes

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