Sodium Hydroxide → 2-(4-Tert-butyldimethylsilyloxymethyl-2-propylphenoxy)-2-phenylacetic acid

HRID 1492630Notes

Reaction equation

HRID 1492630 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:27]=[CH:26][C:13]([O:14][CH:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16]([O:18]C)=[O:17])=[C:12]([CH2:28][CH2:29][CH3:30])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[Si:1]([O:8][CH2:9][C:10]1[CH:27]=[CH:26][C:13]([O:14][CH:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16]([OH:18])=[O:17])=[C:12]([CH2:28][CH2:29][CH3:30])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19385617Methyl 2-(4-tert-butyldimethylsilyloxymethyl-2-propylphenoxy)-2-phenylacetate

Product 1

HCID 193855972-(4-Tert-butyldimethylsilyloxymethyl-2-propylphenoxy)-2-phenylacetic acidYield 51.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.875 g (4.38 mmol) of the product of Step K in methanol (20 mL) was added 1N NaOH (4.82 mL, 4.82 mmol) at rt. The solution was stirred at rt for 3 hours. After the solvent was evaporated under reduced pressure, the residue was dissolved in H2O (30 mL) and washed with ethyl acetate (30 mL). The aqueous layer was acidified to pH=3 with 2N HCl. A milky emulsion was extracted with ethyl acetate (3×). The combined organic layer was washed with brine, and was dried over anhydrous MgSO4. Concentration afforded 0.929 g of the title compound as a colorless glass.

Workup

  1. customAfter the solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in H2O (30 mL)
  3. washwashed with ethyl acetate (30 mL)
  4. extractionA milky emulsion was extracted with ethyl acetate (3×)
  5. washThe combined organic layer was washed with brine
  6. dry with materialwas dried over anhydrous MgSO4
  7. concentrationConcentration

Sources & evidence

ORD record
ord-15dc6df3aba347abbaf2641cdf776588
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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