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2-(p-Isobutylphenyl)acrylic acid-2,2,2-trifluoroethyl ester → Ibuprofen trifluoroethyl ester

HRID 26453
Notes
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Reaction equation

HRID 26453 reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][O:4][C:5](=[O:18])[C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:10][CH:9]=1)=[CH2:7].[H][H]>CO.[C].[Pd]>[F:1][C:2]([F:19])([F:20])[CH2:3][O:4][C:5](=[O:18])[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:16])[CH3:17])=[CH:10][CH:9]=1)[CH3:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 213233102-(p-Isobutylphenyl)acrylic acid-2,2,2-trifluoroethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 21323312Ibuprofen trifluoroethyl esterYield 86.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 2.86 g of 2-(p-isobutylphenyl)acrylic acid-2,2,2-trifluoroethyl ester in 50 ml of methanol was added 0.25 g of palladium-carbon(10%). Hydrogenation was carried out at ordinary temperature and pressure and stopped when a theoretical amount of hydrogen was absorbed. The palladium-carbon was filtered off to give a filtrate. The filtrate was then concentrated in vacuo to yield 2.48 g of 2-(p-isobutylphenyl)propionic acid-2,2,2-trifluoroethyl ester. Mass spectrum: parent ion 288 m/e.

Workup

  1. customwas absorbed
  2. filtrationThe palladium-carbon was filtered off
  3. customto give a filtrate
  4. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-869d3c35f9fe4f3a9df8bfdec348c805
Source dataset
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04150137

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes