4-Oxo-4-(4-phenylsulfanyl-phenyl)-butyric acid → 4-[4-(Phenylsulfanyl)phenyl]butanoic acid

HRID 2103338Notes

Reaction equation

HRID 2103338 reaction equation
O=[C:2]([C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6]>Cl>[C:15]1([S:14][C:11]2[CH:10]=[CH:9][C:8]([CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])=[CH:13][CH:12]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 1

HCID 155947094-Oxo-4-(4-phenylsulfanyl-phenyl)-butyric acid

Product 1

HCID 248345484-[4-(Phenylsulfanyl)phenyl]butanoic acidYield 81.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Powdered Zinc (66 g) was washed with 2% HCl, added to a solution of HgCl2 (6 g) in 50 mL of 6M HCl. This mixture was shaken vigorously for 5 minutes, and excess liquid was decanted. The mixture was then added to a mechanically stirred suspension of 4-oxo-4-(4-phenylsulfanyl-phenyl)-butyric acid (6.5 g, 22.7 mmol) in 450 mL of 6M HCl, and the reaction mixture was stirred at room temperature for 5 days. The mixture was then decanted to remove excess HCl, and quenched by addition of 250 mL water. The aqueous mixture was extracted three times with 100 mL of EtOAc, and the combined organic layers were dried under reduced pressure to yield 5.0 g (18.4 mmol, 81%) of 4-(4-phenylsulfanyl-phenyl)-butyric acid as a crude solid. MS: 273 (M+H)+.

Workup

  1. washPowdered Zinc (66 g) was washed with 2% HCl
  2. additionadded to a solution of HgCl2 (6 g) in 50 mL of 6M HCl
  3. customexcess liquid was decanted
  4. stirringthe reaction mixture was stirred at room temperature for 5 days
  5. customThe mixture was then decanted
  6. customto remove excess HCl
  7. customquenched by addition of 250 mL water
  8. extractionThe aqueous mixture was extracted three times with 100 mL of EtOAc
  9. customthe combined organic layers were dried under reduced pressure

Sources & evidence

ORD record
ord-d3d93fce8fb942d99be2b42412e12b9d
Source dataset
uspto-grants-2009_08
Patent number
US07576103B2

Reaction notes

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