Ethanol → (2,6-Dichlorophenylthio)Acetic Acid

HRID 1906751Notes

Reaction equation

HRID 1906751 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[SH:9].C(O)C.C[O-].[Na+].Br[CH2:17][C:18]([OH:20])=[O:19]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9][CH2:17][C:18]([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 702EthanolHCID 6227Bromoacetic AcidHCID 90671Benzenethiol, 2,6-dichloro-HCID 10942334Sodium Methoxide

Product 1

HCID 1810591(2,6-Dichlorophenylthio)Acetic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,6-dichlorothiophenol, 50 gm, was added to 250 ml of ethanol. 63.8 ml of a 25% solution of sodium methoxide (2 equivalents) in methanol was then added to the system. The system was stirred at room temperature for approximately 3 hours. Afterwards, 20 ml of bromoacetic acid was added and the system then heated to reflux. The system was continued at reflux for 16 hours. The reaction was then stopped and the solvent removed by stripping. The resulting material was dissolved with basic aqueous solution and then washed with methylene chloride. Concentrated HCl was next added to the aqueous solution to acidify it. The product was extracted with methylene chloride. The methylene chloride solution was stripped and triturated with hexane. The product was then filtered, washed with water and air dried to yield 55.3 gm of the title compound.

Workup

  1. temperaturethe system then heated to reflux
  2. temperatureat reflux for 16 hours
  3. customthe solvent removed by stripping
  4. dissolutionThe resulting material was dissolved with basic aqueous solution
  5. washwashed with methylene chloride
  6. additionConcentrated HCl was next added to the aqueous solution
  7. extractionThe product was extracted with methylene chloride
  8. customtriturated with hexane
  9. filtrationThe product was then filtered
  10. washwashed with water and air
  11. customdried

Sources & evidence

ORD record
ord-05870febf8d8440ba4e06e42524d99e0
Source dataset
uspto-grants-1987_03
Patent number
US04654346

Reaction notes

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