Sodium Hydroxide → 2-Methyl-4'-(trifluoromethyl)[1,1'-biphenyl]-4-carboxylic acid

HRID 1669337Notes

Reaction equation

HRID 1669337 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[C:9]([CH3:23])[CH:8]=1)=[O:6]>CO>[CH3:23][C:9]1[CH:8]=[C:7]([C:5]([OH:6])=[O:4])[CH:12]=[CH:11][C:10]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 586102442-Methyl-4'-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester

Product 1

HCID 231205192-Methyl-4'-(trifluoromethyl)[1,1'-biphenyl]-4-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium hydroxide (5.0N, 0.03 mL, 0.15 mmol) to 2-methyl-4′-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester (2.52 g, 8.6 mmol) in methanol (15 mL) and stir for two hours. Acidify with 1.0 N HCl and extract desired compound with ethyl acetate three times. Wash organic phase with saturated sodium chloride solution, dry over Na2SO4, filter and concentrate under reduced pressure to provide 2.31 g (96%) of title compound.

Workup

  1. extractionAcidify with 1.0 N HCl and extract desired compound with ethyl acetate three times
  2. dry with materialWash organic phase with saturated sodium chloride solution, dry over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-208c8c5a64264313a4a6ac3c033f021e
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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