Water → 2-Ethoxy-3-{4-[2-(4-hydroxyphenyl)ethoxy]-3-methylphenyl}propanoic acid

HRID 353306Notes

Reaction equation

HRID 353306 reaction equation
[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26]S(C)(=O)=O)=[CH:22][CH:21]=2)=[C:13]([CH3:31])[CH:12]=1)[C:5]([O:7]CC)=[O:6])[CH3:2].[OH-].[Na+].O>C1COCC1>[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[C:13]([CH3:31])[CH:12]=1)[C:5]([OH:7])=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 22708415Ethyl 2-ethoxy-3-[3-methyl-4-(2-{4-[(methylsulfonyl)oxy]phenyl}ethoxy)phenyl]propanoate

Product 1

HCID 227084062-Ethoxy-3-{4-[2-(4-hydroxyphenyl)ethoxy]-3-methylphenyl}propanoic acidYield 10.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-ethoxy-3-[3-methyl-4-(2-{4-[(methylsulfonyl)oxy]phenyl}ethoxy)phenyl]propanoate (0.150 g; 0.330 mmole) was dissolved in THF. 5M sodium hydroxide (10 eqv) was added and the reaction mixture was stirred over night. Water was added and the THF evaporated. The remaining water was acidified with diluted hydrochloric acid and extracted with ethyl acetate. The organic phase was dried with magnesium sulfate. Purification of the crude product with preparative HPLC (Kromasil C8, 7 μm, 50×250 mm) using acetronitrile (20-100%) in ammonium acetate buffer (pH 7) as mobil phase gave 0.012 g (8% yield) of the desired product.

Workup

  1. customthe THF evaporated
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried with magnesium sulfate
  4. customPurification of the crude product with preparative HPLC (Kromasil C8, 7 μm, 50×250 mm)

Sources & evidence

ORD record
ord-0b04408743a944fd968df7d0042b6706
Source dataset
uspto-grants-2004_06
Patent number
US06750252B2

Reaction notes

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