Sodium Hydroxide → 4'-Fluoro-2-(2-methoxyethoxy)-1,1'-biphenyl-4-carboxylic acid

HRID 494195Notes

Reaction equation

HRID 494195 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16]C)=[O:15])=[CH:10][C:9]=2[O:18][CH2:19][CH2:20][O:21][CH3:22])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][C:9]=2[O:18][CH2:19][CH2:20][O:21][CH3:22])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69039439Methyl 4'-fluoro-2-(2-methoxyethoxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 690396114'-Fluoro-2-(2-methoxyethoxy)-1,1'-biphenyl-4-carboxylic acidYield 11.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 4′-fluoro-2-(2-methoxyethoxy)-1,1′-biphenyl-4-carboxylate (D76) (494 mg) was treated with aq. 2M sodium hydroxide solution (2 ml) in ethanol (3 ml) at 90° C. overnight. After cooling, the ethanol was evaporated off and the residue dissolved in EtOAc and extracted with sat. aq. sodium bicarbonate solution. This was acidified to pH3 with 2M HCl and extracted with EtOAc which was dried over MgSO4 and concentrated in vacuo to give the title compound as a solid (55 mg). MS(ES): M-H+ 289.

Workup

  1. temperatureAfter cooling
  2. customthe ethanol was evaporated off
  3. dissolutionthe residue dissolved in EtOAc
  4. extractionextracted with sat. aq. sodium bicarbonate solution
  5. extractionextracted with EtOAc which
  6. dry with materialwas dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d6bde3cad07401a9de0ebff325799d2
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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