Potassium Carbonate → 5-Benzoyl-indan-2-carboxylic acid

HRID 27922Notes

Reaction equation

HRID 27922 reaction equation
C([O-])([O-])=O.[K+].[K+].[C:7]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[CH2:20][CH:19]([C:24]([O:26]C)=[O:25])[CH2:18]2)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O.CO>[C:7]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[CH2:20][CH:19]([C:24]([OH:26])=[O:25])[CH2:18]2)(=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 23459752Methyl 5-benzoyl-indan-2-carboxylate

Product 1

HCID 234597235-Benzoyl-indan-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a 100 cm3 reaction vessel equipped with a stirrer and a cooler are successively added: 2.2 g (0.026 mole+50%) of potash dissolved in 40 cm3 of water and 7.3 g (0.026 mole) of methyl 5-benzoyl-indane-2-carboxylate dissolved in 40 cm3 of methanol. The mixture is heated at reflux temperature for 1 hour, the methanol evaporated and the mixture diluted with water; the alkaline mixture is then washed with ether and then acidified by the addition of hydrochloric acid. A precipitate forms which is filtered, washed with water and dried. After recrystallization from ethyl acetate the melting point is steady at 140°-142° C. (in a capillary tube).

Workup

  1. customTo a 100 cm3 reaction vessel
  2. customequipped with a stirrer
  3. additiona cooler are successively added
  4. temperatureThe mixture is heated
  5. temperatureat reflux temperature for 1 hour
  6. customthe methanol evaporated
  7. additionthe mixture diluted with water
  8. washthe alkaline mixture is then washed with ether
  9. additionacidified by the addition of hydrochloric acid
  10. filtrationA precipitate forms which is filtered
  11. washwashed with water
  12. customdried
  13. customAfter recrystallization from ethyl acetate the melting point
  14. customis steady at 140°-142° C.

Sources & evidence

ORD record
ord-91ac0706991a43fb99c4dd61e476acfa
Source dataset
uspto-grants-1980_09
Patent number
US04224341

Reaction notes

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