Water → Ibuprofen, (+-)-

HRID 614259Notes

Reaction equation

HRID 614259 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](SC)([CH3:15])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].O.CCOCC>C(O)(=O)C.[Zn]>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:15])[C:12]([OH:14])=[O:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 12917671HCID 12917671, compound

Product 1

HCID 3672Ibuprofen, (+-)-Yield 100.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst3×HCID 176Acetic AcidSolvent

Procedure

α-(p-Isobutylphenyl)-α-(methylthio)propionic acid (387 mg) was dissolved in 3 ml of acetic acid, and 200 mg of zinc powder was added. The mixture was heated under reflux for 2 hours. Furthermore, 200 mg of zinc powder was added, and the mixture was heated under reflux for 18 hours. The zinc powder which agglomerated was pulverized, and the mixture was again heated under reflux for 20 hours. Water (30 ml) and 20 ml of ether were added, and the insoluble matter was separated by filtration. Then, conc. hydrochloric acid was added to adjust the pH of the mixture to 1, and it was extracted four times with 20 ml of diethyl ether. The organic layer was washed with 10 ml of water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the diethyl ether and acetic acid. Thus, 319 mg of α-(p-isobutylphenyl)propionic acid was obtained as an oil which crystallized soon. The yield of the crude product was 100%. Recrystallization from hexane afforded colorless crystals having a melting point of 74° to 76° C. The IR and NMR spectra of ths product were identical with those of the authentic sample.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 18 hours
  5. temperaturethe mixture was again heated
  6. temperatureunder reflux for 20 hours
  7. customthe insoluble matter was separated by filtration
  8. additionThen, conc. hydrochloric acid was added
  9. extractionwas extracted four times with 20 ml of diethyl ether
  10. washThe organic layer was washed with 10 ml of water
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customto remove the diethyl ether and acetic acid

Sources & evidence

ORD record
ord-78b56bfab5a24cdb8bd13cc04b73f6c5
Source dataset
uspto-grants-1979_03
Patent number
US04144248

Reaction notes

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