Thiophenol → Acetic acid, (phenylthio)-, 1,1-dimethylethyl ester

HRID 2253979Notes

Reaction equation

HRID 2253979 reaction equation
[OH-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>O>[C:3]1([S:9][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetate

Product 1

HCID 546353Acetic acid, (phenylthio)-, 1,1-dimethylethyl esterYield 111.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After 2.05 g of sodium hydroxide was dissolved in 50 ml of water, 5.65 g of thiophenol was added to the solution under ice cooling, and the mixture was stirred for a half hour at room temperature. Under ice cooling, 10.0 g of tert-butyl bromoacetate was added to the reaction mixture and the resulting mixture was reacted at room temperature for 3 hours. After completion of the reaction, the reaction mixture was extracted 3 times with ethyl acetate and the extract was washed with saturated sodium chloride aqueous solution. After the ethyl acetate layer was dried over sodium sulfate, ethyl acetate was distilled off to give 12.8 g of crude tert-butyl (phenylthio)acetate.

Workup

  1. customthe resulting mixture was reacted at room temperature for 3 hours
  2. customAfter completion of the reaction
  3. extractionthe reaction mixture was extracted 3 times with ethyl acetate
  4. washthe extract was washed with saturated sodium chloride aqueous solution
  5. dry with materialAfter the ethyl acetate layer was dried over sodium sulfate, ethyl acetate
  6. distillationwas distilled off

Sources & evidence

ORD record
ord-605d788b2507420aafb901d95a035eb3
Source dataset
uspto-grants-1993_08
Patent number
US05233035

Reaction notes

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