Sodium Hydroxide → 5-(Phenyloxy)-2-(trifluoromethyl)benzoic acid

HRID 1946329Notes

Reaction equation

HRID 1946329 reaction equation
[C:1]1([O:7][C:8]2[CH:9]=[CH:10][C:11]([C:18]([F:21])([F:20])[F:19])=[C:12]([CH:17]=2)[C:13]([O:15]C)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([O:7][C:8]2[CH:9]=[CH:10][C:11]([C:18]([F:19])([F:20])[F:21])=[C:12]([CH:17]=2)[C:13]([OH:15])=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66770777Methyl 2-(trifluoromethyl)-5-phenoxybenzoate

Product 1

HCID 595479725-(Phenyloxy)-2-(trifluoromethyl)benzoic acidYield 112.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 5-(phenyloxy)-2-(trifluoromethyl)benzoate (0.504 g, 1.70 mmol) in ethanol (20 ml), was added 2 M aqueous sodium hydroxide (2.0 ml, 4 mmol). The solution was stirred and left to stand overnight. The solvent was evaporated in vacuo. The residue was dissolved in water and diluted with aqueous 2 M HCl. The mixture extracted with chloroform and the phases separated using a hydrophobic frit. The solvent was removed in vacuo to give a colourless oil (0.540 g). The residue was dissolved in chloroform and dried (Na2SO4), filtered and the solvent removed in vacuo to give the title compound as a colourless oil (0.519 g); LCMS: (System 4) (M-H)−=281, tRET=2.84 min.

Workup

  1. waitleft
  2. customThe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. additiondiluted with aqueous 2 M HCl
  5. extractionThe mixture extracted with chloroform
  6. customthe phases separated
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-531e239ace3147e0b5d30fb1258590f8
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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