HCID 521559, compound → 2,5,7-Trimethyl-1-indanone

HRID 1266676Notes

Reaction equation

HRID 1266676 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:6]([CH3:18])([CH3:17])[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[CH3:16])=[O:8]>ClCCl.CCCCCCC>[CH3:17][CH:6]1[CH2:18][C:14]2[C:9](=[C:10]([CH3:16])[CH:11]=[C:12]([CH3:15])[CH:13]=2)[C:7]1=[O:8]

Participants

5

Reactant 2

HCID 521559HCID 521559, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 117690492,5,7-Trimethyl-1-indanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

Aluminium chloride (38 g, 0.29 mole) was suspended in 200 ml of anhydrous dichloromethane. 2-Chloro-2,2′,4′-trimethylpropiophenone (30.0 g, 0.14 mole) in 30 ml of heptane was slowly added to this suspension. During the addition (30 min) the temperature was kept at room temperature. After the addition was completed, the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was poured onto 400 g of ice water, and the organic layer was separated. The organic layer was successively washed twice with a 5 wt % aqueous hydrochloric acid solution (150 ml) and once with a 2 wt % aqueous sodium bicarbonate solution (150 ml). After drying over anhydrous magnesium sulfate the solution was concentrated under reduced pressure. The yield of crude 2,5,7-trimethyl-1-indanone was 22.9 g or 92%. A sample was crystallized from pentane to give crystalline material.

Workup

  1. additionDuring the addition (30 min) the temperature
  2. customwas kept at room temperature
  3. additionAfter the addition
  4. customthe organic layer was separated
  5. washThe organic layer was successively washed twice with a 5 wt % aqueous hydrochloric acid solution (150 ml) and once with a 2 wt % aqueous sodium bicarbonate solution (150 ml)
  6. dry with materialAfter drying over anhydrous magnesium sulfate the solution
  7. concentrationwas concentrated under reduced pressure
  8. customA sample was crystallized from pentane
  9. customto give crystalline material

Sources & evidence

ORD record
ord-c2182886a5ed417490670e58c68781a3
Source dataset
uspto-grants-2003_04
Patent number
US06548710B2

Reaction notes

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