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

HRID 1112418Notes

Reaction equation

HRID 1112418 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 kept under reflux for 6 hrs. It 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 mixture is washed with dilute NaOH, dilute HCl and water, dried and evaporated in vacuo.

Workup

  1. temperatureunder reflux for 6 hrs
  2. filtrationIt is filtered
  3. washthe precipitate is washed with acetone
  4. customthe filtrate is evaporated in vacuo
  5. addition200 ml of ether are added to the residue
  6. washthe mixture is washed with dilute NaOH, dilute HCl and water
  7. customdried
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-d7d6d3fc727046abbd1602278f6286a7
Source dataset
uspto-grants-1978_10
Patent number
US04122186

Reaction notes

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