Hydrochloric Acid → 3-(3-Methylsulfonylamino-4-phenoxyphenoxy)propionic acid

HRID 1031665Notes

Reaction equation

HRID 1031665 reaction equation
[OH-].[Na+].[CH3:3][S:4]([NH:7][C:8]1[CH:9]=[C:10]([OH:21])[CH:11]=[CH:12][C:13]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:6])=[O:5].Cl[CH2:23][CH2:24][C:25]([OH:27])=[O:26].Cl>O.C(OCC)(=O)C>[CH3:3][S:4]([NH:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:21][CH2:23][CH2:24][C:25]([OH:27])=[O:26])(=[O:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 78993-Chloropropionic acidHCID 14798Sodium Hydroxide2×HCID 147222673-Methylsulfonylamino-4-phenoxyphenol

Product 1

HCID 147223063-(3-Methylsulfonylamino-4-phenoxyphenoxy)propionic acidYield 23.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

4 g of sodium hydroxide was dissolved in 250 ml of water. Therein was dissolved 27.9 g of 3-methylsulfonylamino-4-phenoxyphenol. Thereto was added an aqueous solution obtained by dissolving 10.9 g of 3-chloropropionic acid and 4 g of sodium hydroxide in 30 ml of water. The mixture was refluxed for 30 minutes. The reaction mixture was water-cooled and adjusted to pH 8 with 4N hydrochloric acid. 70 ml of ethyl acetate was added thereto. The aqueous layer was separated, adjusted to pH 4 with 4N hydrochloric acid and extracted with 100 ml of ethyl acetate. The resulting extracts were washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was mixed with diethyl ether. The resulting solid was collected by filtration to obtain 8.1 g (yield: 23.1%) of 3-(3-methylsulfonylamino-4-phenoxyphenoxy)propionic acid having a melting point of 145°-149° C.

Workup

  1. additionThereto was added an aqueous solution
  2. customobtained
  3. temperatureThe mixture was refluxed for 30 minutes
  4. temperaturecooled
  5. customThe aqueous layer was separated
  6. extractionextracted with 100 ml of ethyl acetate
  7. washThe resulting extracts were washed with water
  8. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. additionThe residue was mixed with diethyl ether
  11. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-c947a1995bcb4e90ba4336f6bc9cf6e1
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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