Sodium Hydroxide → Ibuprofen, (+-)-

HRID 1658586Notes

Reaction equation

HRID 1658586 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:14])[CH:12]=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[OH-:15].[Na+]>[Ag]=O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:14])[C:12]([OH:15])=[O:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 595156Ibuprofenal

Product 1

HCID 3672Ibuprofen, (+-)-Yield 57%

Reagents, catalysts & solvents 1

HCID 92152Silver(II) oxideCatalyst

Procedure

To a stirred suspension of 1.4 g of silver oxide in 20 ml of 6% aqueous sodium hydroxide was added dropwise 2.1 g of the 2-(4-isobutylphenyl)-propionaldehyde obtained in the procedure of Example 3(i) over 10 minutes at 60°C with stirring. The mixture was further stirred at 60°C for 15 minutes and then allowed to stand. The precipitate was filtered off and washed with hot water. The filtrate and the washing liquor were combined together, and the insoluble oil was removed by extracting with ethyl ether. The remaining aqueous phase was then extracted with ethyl ether, and the ether extract was washed with water, dried and then distilled under reduced pressure to remove the ether. The crude crystalline product so obtained was recrystallised from petroleum benzine, affording 1.3 g of 2-(4-isobutylphenyl)-propionic acid, M.P. 74.8°-76.5°C. Yield 57% (based on the theoretical).

Workup

  1. customobtained in the procedure of Example 3(i) over 10 minutes at 60°C
  2. stirringThe mixture was further stirred at 60°C for 15 minutes
  3. filtrationThe precipitate was filtered off
  4. washwashed with hot water
  5. customthe insoluble oil was removed
  6. extractionby extracting with ethyl ether
  7. extractionThe remaining aqueous phase was then extracted with ethyl ether
  8. extractionthe ether extract
  9. washwas washed with water
  10. customdried
  11. distillationdistilled under reduced pressure
  12. customto remove the ether
  13. customThe crude crystalline product so obtained
  14. customwas recrystallised from petroleum benzine

Sources & evidence

ORD record
ord-3bd4138e06a74d13bbc474d94098c7c4
Source dataset
uspto-grants-1976_06
Patent number
US03965161

Reaction notes

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