2-(4-Isobutylphenyl)acrylic acid → Dexibuprofen

HRID 864689

Reaction equation

HRID 864689 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[CH2:15])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3]>CO>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C@H:11]([CH3:15])[C:12]([OH:14])=[O:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

3

Reactant 1

HCID 111273872-(4-Isobutylphenyl)acrylic acid

Product 1

HCID 39912DexibuprofenYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

In an atmosphere of argon, 4.6 mg (5.4×10-3 mmol) of Ru(OAc)2 [(S)-(-)-OcH-binap] complex and 220.4 mg (1.08 mmol) of 2-(4-isobutylphenyl)-propenoic acid were dissolved in 5.4 ml of methanol, and the resulting solution was put into a 100 ml capacity autoclave and stirred at 25° C. for 24 hours under a hydrogen pressure of 100 atm. The reaction solution was concentrated and then subjected to a silica gel column chromatography (eluting solution, ether) to obtain 211 mg of (S)-2-(4-isobutylphenyl)propionic acid with a yield of 94%.

Workup

  1. concentrationThe reaction solution was concentrated
  2. washsubjected to a silica gel column chromatography (eluting solution, ether)

Sources & evidence

ORD record
ord-917b7a2da0b04a6aab28667ba23a392c
Source dataset
uspto-grants-1996_10
Patent number
US05563295

Linked notes

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