Hydrochloric Acid → HCID 67372061, compound

HRID 1170697Notes

Reaction equation

HRID 1170697 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-a5670502e6314bd5a612ae65db2147be
Source dataset
uspto-grants-2010_11
Patent number
US07825258B2

Reaction notes

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