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

HRID 2083453Notes

Reaction equation

HRID 2083453 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-1b10bba97a8449a19ec8a5ecfc0a40bd
Source dataset
uspto-grants-1978_04
Patent number
US04085219

Reaction notes

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