Potassium Hydroxide → Ketoprofen

HRID 972011Notes

Reaction equation

HRID 972011 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-].[K+]>C(O)C>[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 14797Potassium HydroxideHCID 529083Methyl 2-(3-benzoylphenyl)propanoate

Product 1

HCID 3825Ketoprofen

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The obtained ester (VI-7.5 g.) is dissolved in 75 ml. of ethanol and, under stirring, 3.75 g. of KOH are added. The mixture is stirred for further three hours at ambient temperature and evaporated on a rotation evaporator. The residue is dissolved in 30 ml. of water and extracted with two 10 ml.-portions of chloroform. The aqueous layer is stirred for 15 minutes with 0.8 g. of active carbon and, after the separation of the carbon, it is acidified by means of 5% w./w. HCl. The resinous product is extracted with two 70 ml.-portions of ether and washed with two 50 ml. portions of water. After the drying of the ether extract over Na2SO4, it is evaporated to dryness on a rotation evaporator. Yield: 6.0 g. of a resinous product (84.3% theor.), which is crystallized from acetonitrile.

Workup

  1. customevaporated on a rotation evaporator
  2. dissolutionThe residue is dissolved in 30 ml
  3. extractionof water and extracted with two 10 ml
  4. stirringThe aqueous layer is stirred for 15 minutes with 0.8 g
  5. customof active carbon and, after the separation of the carbon, it
  6. extractionThe resinous product is extracted with two 70 ml
  7. wash-portions of ether and washed with two 50 ml
  8. dry with materialAfter the drying of the ether
  9. extractionextract over Na2SO4, it
  10. customis evaporated to dryness on a rotation evaporator
  11. customof a resinous product (84.3% theor.), which is crystallized from acetonitrile

Sources & evidence

ORD record
ord-f61ff62c993546a699f0b9e01d956d5c
Source dataset
uspto-grants-1979_07
Patent number
US04162364

Reaction notes

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