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Sodium Hydroxide → 4-(4-Methyl-3-thienyl)-3-(trifluoromethyl)benzoic acid

HRID 1950823
Notes
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Reaction equation

HRID 1950823 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][C:10]=2[C:19]([F:22])([F:21])[F:20])=[CH:6][S:7][CH:8]=1>CCO>[CH3:3][C:4]1[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=2[C:19]([F:22])([F:20])[F:21])=[CH:6][S:7][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67528440Methyl 4-(4-methyl-3-thienyl)-3-(trifluoromethyl)benzoate

Product 1

HCID 594958184-(4-Methyl-3-thienyl)-3-(trifluoromethyl)benzoic acidYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydroxide (5M: 6 mL; 30 mmol; 3 eq.) was added to a solution of methyl 4-(4-methyl-3-thienyl)-3-(trifluoromethyl)benzoate (3 g; 10 mmol; 1 eq.) in EtOH (90 mL) and the reaction mixture was stirred at 60° C. for 2 hours. After evaporation of the solvent, the residue was taken up in water (300 mL) and the aqueous phase was washed with ethyl acetate (2×100 mL) then acidified to pH 2 with conc. HCl. The solution was concentrated to ca. 100 mL and extracted with ethyl acetate. The organic layer was dried over magnesium sulphate and concentrated in vacuo to afford the title compound (2.6 g, 91%) as a brown oil.

Workup

  1. customAfter evaporation of the solvent
  2. washthe aqueous phase was washed with ethyl acetate (2×100 mL)
  3. concentrationThe solution was concentrated to ca. 100 mL
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b525ced19acf4ae794332aa8ae082d18
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08404676B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes