Water → Ibuprofen, (+-)-

HRID 1535009Notes

Reaction equation

HRID 1535009 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11](O)[CH3:12])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[OH2:14].C(C1C=CC(C=C)=CC=1)C(C)C.[O:27]1[CH2:32]COCC1>[Rh](I)(I)I>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:12])[C:32]([OH:27])=[O:14])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962Water2×HCID 312751,4-DioxaneHCID 1816541-[4-(2-Methylpropyl)phenyl]ethan-1-ol2×HCID 5761461-Ethenyl-4-(2-methylpropyl)benzene

Product 1

HCID 3672Ibuprofen, (+-)-

Reagents, catalysts & solvents 1

HCID 4428348Rhodium(III) iodideCatalyst

Procedure

A 300-ml autoclave made of Hastelloy was charged with 9.1 g (51.1 mmol) of α-(4-isobutylphenyl) ethyl alcohol, 1.5 g (3.10 mmol) of rhodium iodide, 5.8 g (322 mmol) of water, which gave a concentration of water in the reaction mixture of 2.9 mol/1, and 100 ml of dioxane, as a solvent, to cause a reaction to occur therein under the same conditions as those defined in Example 1. After the completion of the reaction, the gas chromatographic and NMR analysis of the contents indicated that 59% of the α-(4-isobutylphenyl) ethyl alcohol remained unreacted while 40% thereof was converted into 4-isobutylstyrene and α-(4-isobutylphenyl)-propionic acid was formed only in a trace amount.

Workup

  1. customa reaction
  2. customAfter the completion of the reaction

Sources & evidence

ORD record
ord-71e5f532aa7649c59861efe2c109b259
Source dataset
uspto-grants-1992_02
Patent number
US05091563

Reaction notes

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