Water → (4-Chloro-2-{[2-methyl-5-(propylsulfinyl)phenyl]ethynyl}phenoxy)acetic acid

HRID 2390371Notes

Reaction equation

HRID 2390371 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][C:8]([O:10]C)=[O:9])=[C:4]([C:14]#[C:15][C:16]2[CH:21]=[C:20]([S:22]([CH2:24][CH2:25][CH3:26])=[O:23])[CH:19]=[CH:18][C:17]=2[CH3:27])[CH:3]=1.[OH-].[Na+].O>CO>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[C:4]([C:14]#[C:15][C:16]2[CH:21]=[C:20]([S:22]([CH2:24][CH2:25][CH3:26])=[O:23])[CH:19]=[CH:18][C:17]=2[CH3:27])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 56593979Methyl (4-chloro-2-{[2-methyl-5-(propylsulfinyl)phenyl]ethynyl}phenoxy)acetate2×

Product 1

HCID 46865306(4-Chloro-2-{[2-methyl-5-(propylsulfinyl)phenyl]ethynyl}phenoxy)acetic acidYield 83.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl (4-chloro-2-{[2-methyl-5-(propylsulfinyl)phenyl]ethynyl}phenoxy)acetate (Intermediate 221, 125 mg; 0.31 mmol) in MeOH (5 ml) was treated with a 1M solution of sodium hydroxide in water (0.93 ml; 0.93 mmol). After stirring for 3 hours, the solvent was removed under reduced pressure, the residue was taken up in AcOEt and extracted with 0.1N HCl. The organic phase was dried on MgSO4 and concentrated to give a residue which was triturated in diethyl ether, to afford the title compound as a pale yellow solid (101 mg, 83%).

Workup

  1. customthe solvent was removed under reduced pressure
  2. extractionextracted with 0.1N HCl
  3. customThe organic phase was dried on MgSO4
  4. concentrationconcentrated
  5. customto give a residue which
  6. customwas triturated in diethyl ether

Sources & evidence

ORD record
ord-a5562d6582d24551bff8e2ff40c1701b
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

Loading…