Aluminum(III) Chloride → 2,2-Diethyl-5-hydroxy-6,7-dichloro-1-indanone

HRID 1679708Notes

Reaction equation

HRID 1679708 reaction equation
[CH2:1]([C:3]1([CH2:17][CH3:18])[CH2:11][C:10]2[C:5](=[C:6]([Cl:15])[C:7]([Cl:14])=[C:8]([O:12]C)[CH:9]=2)[C:4]1=[O:16])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-]>CCCCCCC>[CH2:17]([C:3]1([CH2:1][CH3:2])[CH2:11][C:10]2[C:5](=[C:6]([Cl:15])[C:7]([Cl:14])=[C:8]([OH:12])[CH:9]=2)[C:4]1=[O:16])[CH3:18]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 203584712,2-Diethyl-5-methoxy-6,7-dichloro-1-indanone

Product 1

HCID 203584452,2-Diethyl-5-hydroxy-6,7-dichloro-1-indanone

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

A stirred suspension of 2,2-diethyl-5-methoxy-6,7-dichloro-1-indanone (4.0 g., 0.014 mole) and aluminum chloride (4.7 g., 0.035 mole) in heptane (150 ml.) is refluxed for one hour and cooled. The heptane is decanted from the reaction mixture and the solid residue is treated with water (200 ml.) and concentrated hydrochloric acid (20 ml.). The 2,2-diethyl-5-hydroxy-6,7-dichloro-1-indanone which separates (3.7 g.) melts at 184° C. after recrystallization from butyl chloride.

Workup

  1. temperatureis refluxed for one hour
  2. temperaturecooled
  3. customThe heptane is decanted from the reaction mixture
  4. additionthe solid residue is treated with water (200 ml.) and concentrated hydrochloric acid (20 ml.)
  5. customafter recrystallization from butyl chloride

Sources & evidence

ORD record
ord-c0aa0cd677554450ac804260f9629791
Source dataset
uspto-grants-1978_03
Patent number
US04081554

Reaction notes

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