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

HRID 219795Notes

Reaction equation

HRID 219795 reaction equation
[CH3:1][C:2]1[C:3]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][C:8]=2[C:17]([F:20])([F:19])[F:18])=[CH:4][S:5][CH:6]=1.[OH-].[Na+]>CCO.O>[CH3:1][C:2]1[C:3]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=2[C:17]([F:20])([F:18])[F:19])=[CH:4][S:5][CH:6]=1

Participants

5

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 90.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of methyl 4-(4-methyl-3-thienyl)-3-(trifluoromethyl)benzoate (3 g; 9.99 mmol; 1 eq.) in EtOH (90 mL) at RT was treated with sodium hydroxide (5.99 mL; 5 M; 29.97 mmol; 3 eq.). The reaction mixture was stirred at 60° C. for 2 hours. The reaction mixture was concentrated to give a brown solid which was taken up in water (300 mL) and the aqueous phase was washed twice with EtOAc. The aqueous phase was acidified with HCl cc to pH 2 and extracted with EtOAc (250 mL). The organic layer was dried over MgSO4 and concentrated affording the title compound as a brown oil (2.60 g, 90%). 1H NMR (DMSO-d6, 300 MHz) δ 13.07 (br s, 1H), 8.34-8.24 (m, 2H), 7.57-7.54 (m, 1H), 7.47-7.46 (m, 1H), 7.34-7.33 (m, 1H), 1.98 (s, 3H). LC/MS (Method A): 284.9 (M−H)−. HPLC (Method A) Rt 4.53 min (Purity: 95.5%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give a brown solid which
  3. washthe aqueous phase was washed twice with EtOAc
  4. extractionextracted with EtOAc (250 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c9a49ed059164e13bcd6b1ad8209bd71
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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