Acetic Acid → 1-Indanone

HRID 37699

Reaktionsgleichung

Reaktionsgleichung von HRID 37699
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([CH3:12])[C:8]2=[O:11])=[CH:4][CH:3]=1.C([CH2:15][C:16]([OH:18])=[O:17])#N.C(O)(=O)C.C1(C)C=CC=CC=1>C(Cl)Cl.C(OCC)(=O)C.O>[OH:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][CH:3]=1)[CH2:6][C:7]([CH3:12])=[C:8]2[CH2:15][C:16]([OH:18])=[O:17].[C:8]1(=[O:11])[C:9]2[C:5](=[CH:4][CH:3]=[CH:2][CH:10]=2)[CH2:6][CH2:7]1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 1140TolueneHCID 9740Cyanoacetic acidHCID 2343386-Hydroxy-2-methyl-2,3-dihydro-1h-inden-1-one

Produkt 2

HCID 67351-IndanoneHCID 199357125-Hydroxy-2-methyl indene-3-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21226138Dichloromethane ethylacetateLösungsmittel

Versuchsvorschrift

A mixture of the indanone (1.81 g, 11.17 mmole)of Example 1, Step D, cyanoacetic acid (1.05 g, 12.3 mmol) ammonium acetate (0.17 g), acetic acid (0.66 g) and toluene (5 mL) is heated at reflux with water removal (Dean-Stark) for 24 hours (TLC, CH2Cl2 -ethyl acetate 8:2). The toluene is evaporated and the residual yellow solid is redissolved in ethanol (6 mL) containing 2.2 N-KOH (1.4 mL). A solution of KOH (2.2 g, 85) in water (15 mL) is added and the solution is refluxed under nitrogen for 18 hours. The ethanol is evaporated, the residue is diluted with water and extracted with ether (2 times). The aqueous layer is acidified in the cold with 6N-HCl (to pH 3) and extracted with ethyl acetate. The extracts are washed with brine, dried (MgSO4) and evaporated to provide the crude title compound together with traces of unreacted indanone. It is used as such in the next step.

Aufarbeitung

  1. temperatureis heated
  2. customThe toluene is evaporated
  3. dissolutionthe residual yellow solid is redissolved in ethanol (6 mL)
  4. additioncontaining 2.2 N-KOH (1.4 mL)
  5. additionA solution of KOH (2.2 g, 85) in water (15 mL) is added
  6. temperaturethe solution is refluxed under nitrogen for 18 hours
  7. customThe ethanol is evaporated
  8. additionthe residue is diluted with water
  9. extractionextracted with ether (2 times)
  10. extractionextracted with ethyl acetate
  11. washThe extracts are washed with brine
  12. dry with materialdried (MgSO4)
  13. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-400c524d3b004716ba7d24f5c33be77b
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420289

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