Water → HCID 12257321, compound

HRID 1169297Notes

Reaction equation

HRID 1169297 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.Br[CH2:11][CH2:12][CH2:13][C:14]([O:16]CC)=[O:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 127654-MethoxybenzenethiolHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 12257321HCID 12257321, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-methoxythiophenol (9.66 g), ethyl 4-bromobutyrate (13.5 g) and potassium carbonate (18.8 g) in DMF (200 ml) was stirred at room temperature for 4 hours. The reaction mixture was mixed with water and was extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated solution of sodium chloride, and was dried with magnesium sulfate. After concentration under reduced pressure, into a solution of the residue in ethanol (200 ml) was added at room temperature a 1 N aqueous solution of sodium hydroxide (85 ml), and the resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was evaporated under reduced pressure to remove the ethanol and was then extracted with diethyl ether. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration under reduced pressure, the precipitated crystals were collected by filtration. The crystals were washed with hexane to obtain 4-[(4-methoxyphenyl)thio]butyric acid (13.09 g) as colorless crystals.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialan aqueous saturated solution of sodium chloride, and was dried with magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. additioninto a solution of the residue in ethanol (200 ml) was added at room temperature a 1 N aqueous solution of sodium hydroxide (85 ml)
  6. customThe reaction mixture was evaporated under reduced pressure
  7. customto remove the ethanol
  8. extractionwas then extracted with diethyl ether
  9. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  10. dry with materialwas dried with magnesium sulfate
  11. concentrationAfter concentration under reduced pressure
  12. filtrationthe precipitated crystals were collected by filtration
  13. washThe crystals were washed with hexane

Sources & evidence

ORD record
ord-b1dca7b6551b4a47a0ea3e30551987b4
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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