Water → 2-[(2-oxopropyl)thio]benzoic acid

HRID 505670Notes

Reaction equation

HRID 505670 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].[C:6]([OH:15])(=[O:14])[C:7]1[C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[SH:9].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[O:5]=[C:3]([CH3:4])[CH2:2][S:9][C:8]1[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=1[C:6]([OH:15])=[O:14]

Participants

7

Reactant 4

HCID 962WaterHCID 54432-Mercaptobenzoic AcidHCID 6571ChloroacetoneHCID 11430Potassium Carbonate

Product 1

HCID 24927392-[(2-oxopropyl)thio]benzoic acidYield 63.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of chloroacetone (5.18 g, 55.99 mmol) in DMF (25 ml) were added thiosalicylic acid (8.63 g, 55.99 mmol) and potassium carbonate (7.74 g, 55.99 mmol), and the mixture was stirred at room temperature for 19 hours. To the reaction solution was added water and ethyl acetate and the mixture was separated by a separating funnel. The aqueous layer was acidified with 1N diluted hydrochloric acid (about pH 4) and extracted with ethyl acetate. Further the organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. After filtration the solvent was removed in vacuo to give the subject compound (7.44 g, 63%).

Workup

  1. customthe mixture was separated by a separating funnel
  2. extractionextracted with ethyl acetate
  3. washFurther the organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration the solvent
  6. customwas removed in vacuo

Sources & evidence

ORD record
ord-9e4b05bae5f043bdb611970b7fa5a15b
Source dataset
uspto-grants-2010_08
Patent number
US07781479B2

Reaction notes

Loading…