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Water → 3,3,3-Trifluoro-2-phenylpropanoic acid

HRID 2393915
Notes
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Reaction equation

HRID 2393915 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(C(F)(F)F)[C:4]([OH:6])=[O:5].[OH-].[Na+].O>CO>[F:1][C:2]([F:17])([F:18])[CH:3]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:4]([OH:6])=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 11821736HCID 11821736, compound

Product 1

HCID 2872493,3,3-Trifluoro-2-phenylpropanoic acidYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

2.9 g (10 millimole) of methyl ester of α,α-bis(trifluoromethyl)phenylacetic acid, 2.5 g (63 millimole) of sodium hydroxide, 3.0 g of water and 3.0 ml of methanol were charged into an eggplant-type flask having a capacity of 100 ml, provided with a marine-type condenser and refluxed at a bath temperature of 90° C. for 6 hours. Methanol was distilled off from the reaction mixture under reduced pressure, and the residue was dissolved in 30 ml of 3N hydrochloric acid and then extracted with ether. The ether layer was dried with anhydrous MgSO4 and then concentrated under reduced pressure. The thus obtained residue was subjected to silica gel column chromatography, using n-hexane/dichloromethane as a mobile phase, whereby 1.26 g of α-(trifluoromethyl)phenylacetic acid was obtained (yield: 62%).

Workup

  1. customprovided with a marine-type condenser
  2. distillationMethanol was distilled off from the reaction mixture under reduced pressure
  3. dissolutionthe residue was dissolved in 30 ml of 3N hydrochloric acid
  4. extractionextracted with ether
  5. dry with materialThe ether layer was dried with anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b03f446834c4d9e85c13d6a3ccc98d8
Source dataset
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05808132

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes