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Hydrochloric Acid → alpha,alpha-Dimethyl-4-(trifluoromethyl)benzenepropanoic acid

HRID 1500236
Notes
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Reaction equation

HRID 1500236 reaction equation
[CH3:1][C:2]([CH3:19])([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)[C:3]([O:5]CC)=[O:4].[OH-].[Na+].Cl>CO>[CH3:1][C:2]([CH3:19])([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][CH:10]=1)[C:3]([OH:5])=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90111330HCID 90111330, compound

Product 1

HCID 62738503alpha,alpha-Dimethyl-4-(trifluoromethyl)benzenepropanoic acidYield 75.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Dissolve ethyl 2,2-dimethyl-3-[4-(trifluoromethyl)phenyl]propanoate (400 mg, 1.46 mmol) in MeOH (2 mL) and add aqueous NaOH solution (3 mL of 3 N). Heat to 80° C. and stir for 3 h. Cool to ambient temperature and acidify with 1 N HCl until pH 4. Extract with EtOAc. Combine organic extracts, wash with brine, dry over sodium sulfate, filter, and concentrate to give the title compound (272 mg).

Workup

  1. temperatureCool to ambient temperature
  2. extractionExtract with EtOAc
  3. washCombine organic extracts, wash with brine
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-018241eabb054d13ba718f99114f0494
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09206139B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes