S-(2-Oxo-1-phenylpropyl) ethanethioate → HCID 13027653, compound

HRID 1032636Notes

Reaction equation

HRID 1032636 reaction equation
[O:1]=[C:2]([CH3:14])[CH:3]([S:10]C(=O)C)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>[OH-].[Na+]>[SH:10][CH:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:2](=[O:1])[CH3:14]

Participants

3

Reactant 1

HCID 14855973S-(2-Oxo-1-phenylpropyl) ethanethioate

Product 1

HCID 13027653HCID 13027653, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Under nitrogen a mixture of 10.6 g (0.05 mol) of ethanethioic acid S-(2-oxo-1-phenylpropyl)ester and 130 ml of 5% sodium hydroxide was stirred rapidly at room temperature for 45 minutes, then extracted with ether. The aqueous mixture was chilled in an ice-bath, acidified with 6N HCl and extracted with ether. The combined organic extracts were washed with brine, dried (MgSO4) and the solvent was removed to give 6.9 g (82%) of crude rac.-1-mercapto-1-phenyl-2-propanone. This compound is sensitive to air and therefore the crude product was used immediately for the condensation reaction.

Workup

  1. extractionextracted with ether
  2. temperatureThe aqueous mixture was chilled in an ice-bath
  3. extractionextracted with ether
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-6803010bfd874365a03165287a837022
Source dataset
uspto-grants-1990_09
Patent number
US04959359

Reaction notes

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