Hydrochloric Acid → 2-(3-Fluoro-4-(methylsulfonyl)phenyl)propanoic acid

HRID 1843006Notes

Reaction equation

HRID 1843006 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]([CH3:17])[C:13]([O:15]C)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[OH-].[Na+].C(OCC)(=O)C.CCCCCC.Cl>CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:12]([CH3:17])[C:13]([OH:15])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21226206Ethyl acetate hexaneHCID 70816532Methyl 2-(3-fluoro-4-(methylsulfonyl)phenyl)propanoate

Product 1

HCID 708157452-(3-Fluoro-4-(methylsulfonyl)phenyl)propanoic acidYield 86.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

To a solution of methyl 2-(3-fluoro-4-(methylsulfonyl)phenyl)propanoate (2.1 g, 0.008 mol) in methanol (21 mL, 10 times), a solution of sodium hydroxide (0.32 g, 1 eq) in water (3 mL) was added at 0° C. The contents were allowed to come to room temperature and the mixture was stirred for 2 h. Progress of the reaction was monitored by TLC (50% ethyl acetate/hexane, Rf˜0.1). On completion of the reaction, methanol was distilled off completely and the residue obtained was taken in water. The contents were acidified to a pH of 4 with diluted HCl, the precipitate was filtered and dried to yield 2-(3-fluoro-4-(methylsulfonyl)phenyl)propanoic acid as a white colored solid (1.7 g, 85%).

Workup

  1. customto come to room temperature
  2. distillationwas distilled off completely
  3. customthe residue obtained
  4. filtrationthe precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-5cd0ded4498e4cae9fb91d83295e7f60
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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