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

HRID 1287429Notes

Reaction equation

HRID 1287429 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 one 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 (50 ml.). The product which separates (7.6 g.) melts at 273° C. after crystallization from nitromethane.

Workup

  1. temperatureis refluxed for one 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 (50 ml.)
  5. customafter crystallization from nitromethane

Sources & evidence

ORD record
ord-2caae4e9b826455faf32ac7978c7918d
Source dataset
uspto-grants-1976_10
Patent number
US03984465

Reaction notes

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