Aluminum(III) Chloride → 6,7-Dichloro-5-hydroxy-2,2-dimethyl-indan-1-one

HRID 597002Notes

Reaction equation

HRID 597002 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:10][C:9]2[C:4](=[C:5]([Cl:14])[C:6]([Cl:13])=[C:7]([O:11]C)[CH:8]=2)[C:3]1=[O:15].[Cl-].[Al+3].[Cl-].[Cl-]>CCCCCCC>[CH3:1][C:2]1([CH3:16])[CH2:10][C:9]2[C:4](=[C:5]([Cl:14])[C:6]([Cl:13])=[C:7]([OH:11])[CH:8]=2)[C:3]1=[O:15]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 123955652,2-Dimethyl-5-methoxy-6,7-dichloro-1-indanone

Product 1

HCID 123955876,7-Dichloro-5-hydroxy-2,2-dimethyl-indan-1-one

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

A stirred suspension of 2,2-dimethyl-5-methoxy-6,7-dichloro-1-indanone (12.2 g., 0.047 mole) and aluminum chloride (15.5 g., 0.116 mole) in heptane (500 ml.) is refluxed for 1 hour and cooled. The heptane is decanted from the reaction mixture and the solid residue is poured into ice (500 g.) and concentrated hydrochloric acid (50ml.). The product which separates (7.6 g.) melts at 273° C. after crystallization from nitromethane.

Workup

  1. temperatureis refluxed for 1 hour
  2. temperaturecooled
  3. customThe heptane is decanted from the reaction mixture
  4. additionthe solid residue is poured into ice (500 g.) and concentrated hydrochloric acid (50ml.)
  5. customafter crystallization from nitromethane

Sources & evidence

ORD record
ord-73910ee7da494611b814eded18e97b15
Source dataset
uspto-grants-1977_03
Patent number
US04012524

Reaction notes

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