Sodium Hydroxide → 3-Fluoro-5-(3-fluorophenyl)-2-methyl-benzoic acid

HRID 1771729Notes

Reaction equation

HRID 1771729 reaction equation
[F:1][C:2]1[C:3]([CH3:19])=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:11]=1)[C:5]([O:7]C)=[O:6].[OH-].[Na+]>C1COCC1.CO>[F:1][C:2]1[C:3]([CH3:19])=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:11]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 89443724Methyl 3-fluoro-5-(3-fluorophenyl)-2-methyl-benzoate

Product 1

HCID 894451373-Fluoro-5-(3-fluorophenyl)-2-methyl-benzoic acidYield 143%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-fluoro-5-(3-fluorophenyl)-2-methyl-benzoate (1.0 g, 3.1 mmol, 1.0 eq) in a mixture of THF (4 mL) and MeOH (4 mL) was added NaOH (2 M aqueous solution, 10 mL, 20 mmol). The reaction mixture was stirred at room temperature for 3 h. The THF and MeOH were evaporated in vacuo and the pH of the aqueous phase was adjusted to pH 4-6 by addition of diluted HCl. The solid precipitate that formed was collected by filtration, washed with water and dried to give the title compound as a white solid (1.1 g, 100%).

Workup

  1. customThe THF and MeOH were evaporated in vacuo
  2. additionthe pH of the aqueous phase was adjusted to pH 4-6 by addition of diluted HCl
  3. customThe solid precipitate that formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-56436c33ec6449dd902d957d52feec60
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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