Lithium hydroxide, monohydrate → 2-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoic acid

HRID 2212993Notes

Reaction equation

HRID 2212993 reaction equation
O.[OH-].[Li+].[CH3:4][C:5]([CH3:24])([C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1)[C:6]([O:8]C)=[O:7]>CO.O.O1CCCC1>[CH3:4][C:5]([CH3:24])([C:10]1[CH:11]=[C:12]([C:20]([F:21])([F:22])[F:23])[CH:13]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=1)[C:6]([OH:8])=[O:7]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 219553242-(3,5-Bis-trifluoromethyl-phenyl)-2-methylpropionic acid, methyl ester

Product 1

HCID 98359482-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoic acidYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (2.13 g, 50.6 mmol) was added to a suspension of methyl α,α-dimethyl-3,5-bis(trifluoromethyl)benzeneacetate (Description 5, 5.3 g, 16.88 mmol) in methanol (60 mL), water (20 mL) and tetrahydrofuran (20 mL) and the mixture was degassed and stirred at room temperature for 3 days. The solvent was evaporated under reduced pressure and the residue was suspended in hydrochloric acid (1M). The mixture was extracted with ethyl acetate and the combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colorless solid (5.05 g, 100%). 1H NMR (400 MHz, CDCl3) δ 7.84 (2H, s), 7.80 (1H, s), and 1.68 (6H, s).

Workup

  1. customthe mixture was degassed
  2. customThe solvent was evaporated under reduced pressure
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe combined organic fractions were dried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-75c20058343841b7aa0b3485e6291398
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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