Water → HCID 20246850, compound

HRID 1589357Notes

Reaction equation

HRID 1589357 reaction equation
Br[C:2]1([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]1=[O:18].[OH2:26]>[N+]([O-])([O-])=O.[Ag+]>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([C:2]2([OH:26])[C:10](=[O:11])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][C:8]=3[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:3]2=[O:18])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 962WaterHCID 20246842HCID 20246842, compound

Product 1

HCID 20246850HCID 20246850, compound

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

A mixture of 2-bromo-2-(p-chlorophenyl)-4-phenylindane-1,3-dione (0.3 g), silver nitrate (0.15 g) ethanol (3 ml) and water (3 ml) was heated under reflux for 2 hours. After cooling, the precipitated solid was filtered off. The solvent was removed from the filtrate under reduced pressure and the residual solid was chromatographed in silica. Recrystallisation from ethanol-water of the fraction eluted with ethyl acetate afforded 2-(p-chlorophenyl)-2-hydroxy-4-phenylindane-1,3-dione, m.p. 161-163.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitated solid was filtered off
  5. customThe solvent was removed from the filtrate under reduced pressure
  6. customthe residual solid was chromatographed in silica
  7. customRecrystallisation from ethanol-water of the fraction
  8. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-24eefafd273e41a59ea8ebedf4409b9f
Source dataset
uspto-grants-1986_02
Patent number
US04569945

Reaction notes

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