Sodium Hydroxide → 2-(3,5-Bis(trifluoromethyl)phenyl)propanoic acid

HRID 2212992Notes

Reaction equation

HRID 2212992 reaction equation
[OH-].[Na+].[CH3:3][CH:4]([C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([C:19]([F:22])([F:21])[F:20])[CH:10]=1)[C:5]([O:7]C)=[O:6]>CO>[CH3:3][CH:4]([C:9]1[CH:10]=[C:11]([C:19]([F:20])([F:21])[F:22])[CH:12]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:14]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21955130(RS)-Methyl alpha-Methyl-3,5-bis(trifluoromethyl)benzeneacetate

Product 1

HCID 115220582-(3,5-Bis(trifluoromethyl)phenyl)propanoic acidYield 100.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous sodium hydroxide (4M, 3 mL, 12 mmol) was added to a solution of (RS)-methyl α-methyl-3,5-bis(trifluoromethyl)benzeneacetate (Description 3, 0.96 g, 3.2 mmol) in methanol (5 mL) and the mixture was heated under reflux for 1 hour. The mixture was cooled and the solvent was evaporated under reduced pressure. The residue was diluted with water, acidified with hydrochloric acid (2M) and extracted with ethyl acetate (2×25 mL). The combined organic fractions were washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colorless solid (0.92 g, 99%). 1H NMR (360 MHz, CDCl3) δ 1.60 (3H, d, J 7.2 Hz), 3.90 (1H, q, J 7.2 Hz), 7.78 (2H, s) and 7.81 (1H, s).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe mixture was cooled
  4. customthe solvent was evaporated under reduced pressure
  5. additionThe residue was diluted with water
  6. extractionextracted with ethyl acetate (2×25 mL)
  7. washThe combined organic fractions were washed with brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c0e88ae441b94c4a9343e574af9bf4ca
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

Loading…