Iodine → Ibuprofen, (+-)-

HRID 1905552Notes

Reaction equation

HRID 1905552 reaction equation
[C]=[O:2].[CH2:3]([C:7]1[CH:12]=[CH:11][C:10]([CH:13](O)[CH3:14])=[CH:9][CH:8]=1)[CH:4]([CH3:6])[CH3:5].II.[O:18]1[CH2:23]COCC1>[Cr].[Co].[Rh](I)(I)I>[CH2:3]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:14])[C:23]([OH:18])=[O:2])=[CH:9][CH:8]=1)[CH:4]([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 807IodineHCID 312751,4-DioxaneHCID 1816541-[4-(2-Methylpropyl)phenyl]ethan-1-olHCID 178418416HCID 178418416, compound

Product 1

HCID 3672Ibuprofen, (+-)-

Reagents, catalysts & solvents 2

HCID 4428348Rhodium(III) iodideCatalystHCID 11332432Hastelloy CCatalyst

Procedure

A 300-ml autoclave made of Hastelloy C was charged with 1.5 g (3.10 mmol) of rhodium iodide and 100 ml of dioxane, as a solvent, to cause a reaction to occur therein under a hydrogen pressure of 10 kg/cm2 and a carbon monoxide pressure of 30 kg/cm2 at 150° C. with stirring. After cooling the reaction mixture and relieving the pressure, 8.9 g (50.0 mmol) of α-(4-isobutylphenyl)ethyl alcohol and 0.40 g (3.15 mmol) of iodine were further added thereto and then the procedure of Example 1 was repeated. Thus 4.5 g of α-(4-isobutylphenyl)propionic acid was obtained.

Workup

  1. customa reaction
  2. temperatureAfter cooling the reaction mixture
  3. additionwere further added

Sources & evidence

ORD record
ord-ba8d917c913a443fa1d50ef643c4aa16
Source dataset
uspto-grants-1989_06
Patent number
US04843172

Reaction notes

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