Aluminum(III) Chloride → 4-Fluoro-7-hydroxy-2,3-dihydro-1H-inden-1-one

HRID 1492954Notes

Reaction equation

HRID 1492954 reaction equation
[CH:1]1[C:6]([O:7]C(CCCl)=O)=[CH:5][CH:4]=[C:3]([F:13])[CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-]>O>[F:13][C:3]1[CH:2]=[CH:1][C:6]([OH:7])=[C:5]2[C:4]=1[CH2:4][CH2:5][C:6]2=[O:7]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 14069823HCID 14069823, compound

Product 1

HCID 152684884-Fluoro-7-hydroxy-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Compound I (219 g) is slowly added to anhydrous AlCl3 (720 g) under nitrogen and kept at room temperature while stirred. Stirring is discontinued when the mixture becomes too viscous. After heating to 120° C. for 1 h, stirring is re-started again and the temperature is further increased to 180° C. (2 hrs). After cooling and addition of excess water, the product is steam-distilled. Extraction with chloroform and evaporation gives 127 g of crude II.

Workup

  1. customkept at room temperature
  2. stirringStirring
  3. stirringstirring
  4. temperaturethe temperature is further increased to 180° C. (2 hrs)
  5. temperatureAfter cooling
  6. distillationthe product is steam-distilled
  7. extractionExtraction
  8. customwith chloroform and evaporation

Sources & evidence

ORD record
ord-afb609d74d5a49ec9e7f449a78863210
Source dataset
uspto-grants-1994_12
Patent number
US05376687

Reaction notes

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