Aluminum(III) Chloride → HCID 12395576, compound

HRID 597030Notes

Reaction equation

HRID 597030 reaction equation
[CH2:1]([CH:3]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[C:5](=[C:6]([Cl:21])[C:7]([Cl:20])=[C:8]([O:18]C)[CH:9]=2)[C:4]1=[O:22])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-]>CCCCCCC>[CH2:1]([CH:3]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[C:5](=[C:6]([Cl:21])[C:7]([Cl:20])=[C:8]([OH:18])[CH:9]=2)[C:4]1=[O:22])[CH3:2]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 12395569HCID 12395569, compound

Product 1

HCID 12395576HCID 12395576, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

A stirred mixture of 2-ethyl-3-phenyl-5-methoxy-6,7-dichloro-1-indanone (13.9 g., 0.0415 mole) and aluminum chloride (13.6 g., 0.104 mole) in heptane (120 ml. is refluxed for five hours then cooled. The heptane is decanted, and the residue is treated with ice water (100 ml.) containing hydrochloric acid. The gum which separates is extracted into ether, washed with water, dried over magnesium sulfate, and the ether evaporated at reduced pressure affording 11.3 g. of 2-ethyl-3-phenyl-5-hydroxy-6,7-dichloro-1-indanone which melts at 220°-222° C. after recrystallization from methanol.

Workup

  1. temperatureis refluxed for five hours
  2. temperaturethen cooled
  3. customThe heptane is decanted
  4. additionthe residue is treated with ice water (100 ml.)
  5. additioncontaining hydrochloric acid
  6. extractionThe gum which separates is extracted into ether
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. customthe ether evaporated at reduced pressure
  10. customaffording 11.3 g
  11. customof 2-ethyl-3-phenyl-5-hydroxy-6,7-dichloro-1-indanone which melts at 220°-222° C. after recrystallization from methanol

Sources & evidence

ORD record
ord-5582d8b085fe495fb0e0dd9fb6a92630
Source dataset
uspto-grants-1977_03
Patent number
US04012524

Reaction notes

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