Sodium Hydroxide → (4-Cyclopropylsulfanylphenyl)oxoacetic acid

HRID 19965Notes

Reaction equation

HRID 19965 reaction equation
[OH-].[Na+].[CH:3]1([S:6][C:7]2[CH:12]=[CH:11][C:10]([C:13](=[O:19])[C:14]([O:16]CC)=[O:15])=[CH:9][CH:8]=2)[CH2:5][CH2:4]1>CCO>[CH:3]1([S:6][C:7]2[CH:8]=[CH:9][C:10]([C:13](=[O:19])[C:14]([OH:16])=[O:15])=[CH:11][CH:12]=2)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 46856411Ethyl [4-(cyclopropylsulfanyl)phenyl](oxo)acetate

Product 1

HCID 21094072(4-Cyclopropylsulfanylphenyl)oxoacetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

2M aqueous NaOH (163 ml) was added to a solution of ethyl (4-cyclopropylsulfanylphenyl)oxoacetate (40.62 g, 162.5 mmol) in EtOH (200 ml) and the stirred mixture heated at 60° C. for 2 h. After cooling, the mixture was concentrated to 150 ml and washed with ether (2×100 ml). Sufficient concentrated HCl was then added to adjust the pH to 1 and the resulting precipitate was extracted into EtOAc (2×300 ml). The combined organic phases were washed with water (3×100 ml), brine (200 ml) and dried (MgSO4). Removal of the solvent afforded the title compound: m/z (ES−)=221.0 [M−H+]−.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated to 150 ml
  3. washwashed with ether (2×100 ml)
  4. additionSufficient concentrated HCl was then added
  5. extractionthe resulting precipitate was extracted into EtOAc (2×300 ml)
  6. washThe combined organic phases were washed with water (3×100 ml), brine (200 ml)
  7. dry with materialdried (MgSO4)
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-e7d758d2a78a4b3faea42592576a471c
Source dataset
uspto-grants-2010_06
Patent number
US07745491B2

Reaction notes

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