Hydrochloric Acid → HCID 67372061, compound

HRID 1678810Notes

Reaction equation

HRID 1678810 reaction equation
C([O:3][C:4](=[O:19])[CH:5]([C:8]1[C:13]([F:14])=[CH:12][C:11]([O:15][CH2:16][CH3:17])=[CH:10][C:9]=1[F:18])[O:6][CH3:7])C.[Li+].[OH-].Cl>C1COCC1.CO>[CH2:16]([O:15][C:11]1[CH:10]=[C:9]([F:18])[C:8]([CH:5]([O:6][CH3:7])[C:4]([OH:19])=[O:3])=[C:13]([F:14])[CH:12]=1)[CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67370552HCID 67370552, compound

Product 1

HCID 67372061HCID 67372061, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To (4-ethoxy-2,6-difluoro-phenyl)-methoxy-acetic acid ethyl ester (4.0 g, 14.58 mmol, 1.0 equiv), dissolved in THF (75 mL) and methanol (15 mL), was added a solution of 1 M LiOH (17.5 mL) and the reaction mixture stirred at rt for 4 h. A solution of 1 M HCl (25 mL) was added, the organic solvents removed by evaporation under reduced pressure and the residue extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4 and concentrated by evaporation under reduced pressure yielding 3.5 g (98%) of the title compound.

Workup

  1. customthe organic solvents removed by evaporation under reduced pressure
  2. extractionthe residue extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-2b088e528f72469186803975aa84ba52
Source dataset
uspto-grants-2011_08
Patent number
US08008503B2

Reaction notes

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