Sodium Hydroxide → Ketoprofen

HRID 1835623Notes

Reaction equation

HRID 1835623 reaction equation
C[O:2][C:3](=[O:20])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)[CH3:5].[OH-].[Na+]>CO>[C:12]([C:8]1[CH:7]=[C:6]([CH:4]([CH3:5])[C:3]([OH:20])=[O:2])[CH:11]=[CH:10][CH:9]=1)(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 529083Methyl 2-(3-benzoylphenyl)propanoate

Product 1

HCID 3825KetoprofenYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of (5) (2.4 g, 0.009 mol) in methyl alcohol (25 ml) was added with 1N NaOH (13.5 ml) and the mixture was left under stirring for 8 hours at room temperature. After evaporating the solvent, the residue was diluted with water and 5% monobasic sodium phosphate was added drop by drop to the mixture to adjust pH to 5. The aqueous layer was then extracted with methyl acetate (2×100 ml). The collected organic extracts were dried over Na2SO4 and evaporated under vacuum, then crystallized from a benzene/petroleum ether 6:20 mixture to obtain 2.05 g of (6) (0.0081 mol; yield 90%) as a white solid (melting point 92-92° C.) following crystallization.

Workup

  1. waitthe mixture was left
  2. customAfter evaporating the solvent
  3. additionthe residue was diluted with water and 5% monobasic sodium phosphate
  4. additionwas added drop by drop to the mixture
  5. extractionThe aqueous layer was then extracted with methyl acetate (2×100 ml)
  6. dry with materialThe collected organic extracts were dried over Na2SO4
  7. customevaporated under vacuum
  8. customcrystallized from a benzene/petroleum ether 6:20 mixture

Sources & evidence

ORD record
ord-d400c7f23577417388b09350595683b6
Source dataset
uspto-grants-2004_08
Patent number
US06770781B1

Reaction notes

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