Potassium Hydroxide → 2-Phenoxyethyl (acetylsulfanyl)acetate

HRID 259296Notes

Reaction equation

HRID 259296 reaction equation
[OH-].[K+].[C:3]([OH:6])(=[S:5])[CH3:4].Br[CH2:8][C:9]([O:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10]>O.CC(C)=O>[C:3]([S:5][CH2:8][C:9]([O:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10])(=[O:6])[CH3:4]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 3474092-Phenoxyethyl bromoacetateHCID 178418634HCID 178418634, compound

Product 1

HCID 541591052-Phenoxyethyl (acetylsulfanyl)acetateYield 98.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

The solution of potassium hydroxide (6.6g) in water (20 ml) was added under ice cooling to thioacetic acid (7.6g) and then the solution of β-phenoxyethyl bromoacetate (25.9g) in acetone (30ml) was added and treated for 6 hours at room temperature. Extracted twice with 200 ml of ethylether and the ether layer was washed with water, dried, and concentrated, giving colourless crystals (24.9g) which was then recrystallized from n-hexane. Thus colourless crystals (20.8g), m.p. 56.0°-57.0° C., of β-phenoxyethyl S-acetylthioglycolate was obtained.

Workup

  1. additiontreated for 6 hours at room temperature
  2. extractionExtracted twice with 200 ml of ethylether
  3. washthe ether layer was washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a4c00797576f4647b41e6e2ea1e96ef9
Source dataset
uspto-grants-1977_07
Patent number
US04036984

Reaction notes

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