Hydrochloric Acid → 2-[(4-Acetylphenyl)sulfanyl]acetic acid

HRID 1394629Notes

Reaction equation

HRID 1394629 reaction equation
C[O:2][C:3](=[O:15])[CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][CH:7]=1.[Li+].[OH-].Cl>C1COCC1.O>[C:12]([C:9]1[CH:8]=[CH:7][C:6]([S:5][CH2:4][C:3]([OH:15])=[O:2])=[CH:11][CH:10]=1)(=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 16741950HCID 16741950, compound

Product 1

HCID 144040822-[(4-Acetylphenyl)sulfanyl]acetic acidYield 91.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(4-Acetyl-phenylsulfanyl)-acetic acid methyl ester (1.48 g, 6.6 mmol) is dissolved in THF (40 ml). To this solution is added LiOH (415 mg, 9.9 mmol) in water (10 ml), and the mixture was stirred at ambient temperature overnight. The mixture was acidified to pH 5 using 1N HCl and then extracted with ethyl acetate (3×25 ml). The combined organic layers were dried over MgSO4 and concentrated in vacuo to yield (4-acetyl-phenylsulfanyl)-acetic acid as a white solid (1.27 g, 91%).

Workup

  1. extractionextracted with ethyl acetate (3×25 ml)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05a509e742ff42c28946960fd75c152b
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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