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

HRID 1287434Notes

Reaction equation

HRID 1287434 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 recrystalization 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 recrystalization from butyl chloride

Sources & evidence

ORD record
ord-c68f2c89f62a4a999118c662bce96b20
Source dataset
uspto-grants-1976_10
Patent number
US03984465

Reaction notes

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