Water → [1,1'-Biphenyl]-2-carboxylic acid, 6-methyl-4'-(trifluoromethyl)-

HRID 1814771Notes

Reaction equation

HRID 1814771 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([C:18]([O:20]C)=[O:19])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.[OH-].[Na+].O>C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([C:18]([OH:20])=[O:19])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:16])([F:17])[F:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 11833278Methyl 6-methyl-4'-trifluoromethylbiphenyl-2-carboxylate

Product 1

HCID 10945826[1,1'-Biphenyl]-2-carboxylic acid, 6-methyl-4'-(trifluoromethyl)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 6-methyl-4′-trifluoromethyl-1,1′-biphenyl-2-carboxylate (13.6 g, 46.3 mmol), and 1N NaOH (92.5 mL, 92.5 mmol) in 225 mL of ethanol is refluxed for 5 h. Water is added to the mixture and the aqueous layer is washed with ether. The aqueous layer is acidified with 1N HCl and extracted with ethyl acetate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The product is purified by crystallization from ethyl acetate/hexanes to yield 6-methyl-4′-trifluoromethyl-1,1′-biphenyl-2-carboxylic acid melting at 202-203° C. 1HNMR CDCl3: 300 MHz): δ 7.87 (1H, d), 7.65 (2H, d), 7.47 (1H, d), 7.35 (1H, t), 7.25 (2H, d), 2.05 (3H, s). MS m/z 279 (M−1).

Workup

  1. temperatureis refluxed for 5 h
  2. washthe aqueous layer is washed with ether
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe product is purified by crystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9ef3a7e91efb474dba7d3872be1a94aa
Source dataset
uspto-grants-2005_04
Patent number
US06878707B2

Reaction notes

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