Lithium Hydroxide → 2-Isopropoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)phenyl]propanoic acid

HRID 987340Notes

Reaction equation

HRID 987340 reaction equation
C[O:2][C:3](=[O:30])[CH:4]([O:26][CH:27]([CH3:29])[CH3:28])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=2)=[CH:8][CH:7]=1.[OH-].[Li+]>O1CCCC1.O>[CH:27]([O:26][CH:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:19][CH:20]=2)=[CH:8][CH:7]=1)[C:3]([OH:30])=[O:2])([CH3:28])[CH3:29]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 572273272-Isopropoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)phenyl]propanoic acid methyl ester

Product 1

HCID 229887122-Isopropoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)phenyl]propanoic acidYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Isopropoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)phenyl]propanoic acid methyl ester (0.1 g; 0.229 mmole) was dissolved in tetrahydrofuran(2 ml). Lithium hydroxide (0.006 g; 0.25 mmole) in water (2 ml) was added. The reaction mixture was stirred at room temperature for 8 hours. Tetrahydrofuran was evaporated. The remaining water solution was extracted with diethyl ether. The water solution was then acidified with hydorchloric acid (1%) to pH˜2 and extracted twice with ethyl acetate. The organic phases were combined and dried with magnesium sulfate. The solvent was evaporated and 0.085 g (88% yield) of 2-isopropoxy-3-[4-(2-{4-methylsulfonyloxyphenyl}ethoxy)phenyl]propanoic acid was obtained.

Workup

  1. customTetrahydrofuran was evaporated
  2. extractionThe remaining water solution was extracted with diethyl ether
  3. extractionextracted twice with ethyl acetate
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ae5fbe511fc240fa97b44b1194588fba
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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