Hydrochloric Acid → 3-Methyl-4-[2-(trifluoromethyl)phenyl]benzoic acid

HRID 2215111Notes

Reaction equation

HRID 2215111 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])=[C:7]([CH3:21])[CH:6]=1)=[O:4].[OH-].[Na+].Cl>O1CCCC1>[CH3:21][C:7]1[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[CH:9][C:8]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([F:18])([F:19])[F:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59606539Methyl 2-methyl-2'-(trifluoromethyl)biphenyl-4-carboxylate

Product 1

HCID 219478123-Methyl-4-[2-(trifluoromethyl)phenyl]benzoic acidYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-methyl-2′-trifluoromethyl-[1,1′-biphenyl]-4-yl)carboxylic acid methyl ester of Step B (1.9 g, 6.5 mmol) in tetrahydrofuran (30 mL) was added 1 N sodium hydroxide (13 mL, 13 mmol). The reaction mixture was heated at reflux overnight, then cooled and acidified with 2 N hydrochloric acid. The aqueous layer was extracted with ethyl acetate and the combined extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 1.65 g of the title compound as a white solid, m.p. 171–174° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperaturecooled
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2fa47809d5e04b13ba96bdb4894cec7b
Source dataset
uspto-grants-2006_09
Patent number
US07109193B2

Reaction notes

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