Potassium Iodide → Ethyl 2-(p-chlorobenzylthio)-propionate

HRID 2285933Notes

Reaction equation

HRID 2285933 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][SH:7])=[CH:4][CH:3]=1.Br[CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][S:7][CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 804094-Chlorobenzyl mercaptan

Product 1

HCID 20542836Ethyl 2-(p-chlorobenzylthio)-propionate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 19.5 ml (0.15 mol) of 4-chlorobenzylmercaptan, 27.1 g (0.15 mol) of ethyl α-bromopropionate, 21 g of potassium carbonate and 0.1 g of potassium iodide in 100 ml of anhydrous acetone is maintained under reflux for 6 hours. The mixture is filtered, the precipitate is washed with acetone and the filtrate is evaporated in vacuo. 200 ml of ether are added to the residue and the ether solution is washed with dilute NaOH, dilute HCl and water.

Workup

  1. temperatureis maintained
  2. temperatureunder reflux for 6 hours
  3. filtrationThe mixture is filtered
  4. washthe precipitate is washed with acetone
  5. customthe filtrate is evaporated in vacuo
  6. addition200 ml of ether are added to the residue
  7. washthe ether solution is washed with dilute NaOH, dilute HCl and water

Sources & evidence

ORD record
ord-5472212f432d4beba764cd8dbad7740b
Source dataset
uspto-grants-1982_04
Patent number
US04325964

Reaction notes

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