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Methanol → 4,4,4-Trifluorobutanoic acid

HRID 399314
Notes
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Reaction equation

HRID 399314 reaction equation
[F:1][C:2]([F:11])([F:10])[CH2:3][CH2:4][C:5]([O:7]CC)=[O:6].[OH-].[K+].CO>O>[F:1][C:2]([F:11])([F:10])[CH2:3][CH2:4][C:5]([OH:7])=[O:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 2733273Ethyl 4,4,4-Trifluorobutyrate

Product 1

HCID 27770854,4,4-Trifluorobutanoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 160 g of ethyl 4,4,4-trifluorobutyrate, a mixed solution of 123 g of potassium hydroxide, 900 ml of methanol and 80 ml of water was added under ice cooling and the mixture was further reacted at room temperature for 12 hours. After the reaction solution was concentrated under reduced pressure, the resulting residue was then partitioned between water and diethyl ether. The ether layer was extracted once with water and the water layer was combined with the aqueous layer which had already been partitioned. After adjusting the pH to about 1 by the addition of an aqueous 10% ice-cooled hydrochloric acid solution, the mixture was extracted three times with diethyl ether. The layers were combined and the combined ether layer was washed twice with saturated saline and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to give 131 g of 4,4,4-trifluorobutyric acid (yield: 98%).

Workup

  1. customthe mixture was further reacted at room temperature for 12 hours
  2. concentrationAfter the reaction solution was concentrated under reduced pressure
  3. customthe resulting residue was then partitioned between water and diethyl ether
  4. extractionThe ether layer was extracted once with water
  5. customhad already been partitioned
  6. additionby the addition of an aqueous 10% ice-
  7. temperaturecooled hydrochloric acid solution
  8. extractionthe mixture was extracted three times with diethyl ether
  9. washthe combined ether layer was washed twice with saturated saline
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1de14fe6cafc4f108fc870d9f9d65998
Source dataset
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05817880

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes