Acetyl chloride → 2-Acetyl-1,1,3,5-tetramethylindene

HRID 479296Notes

Reaction equation

HRID 479296 reaction equation
CC1(C)[C:10]2[C:5](=[CH:6][C:7]([CH3:11])=[CH:8]C=2)[CH:4]([CH2:12][C:13]2C=C[C:16](C)=[CH:15][CH:14]=2)[CH:3]1C.[Cl-].[Cl-].[Cl-].[Al+3].[C:26](Cl)(=[O:28])[CH3:27]>ClCCCl>[C:26]([C:6]1[C:7]([CH3:8])([CH3:11])[C:12]2[C:4]([C:5]=1[CH3:10])=[CH:3][C:15]([CH3:16])=[CH:14][CH:13]=2)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 11818283HCID 11818283, compound

Product 1

HCID 112528792-Acetyl-1,1,3,5-tetramethylindeneYield 34.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
29 °C

Procedure

To a mixture of 50.8 g 90.8% pure 1,1,2,5-tetramethyl-3-(4-methyl-benzyl)indane and 52.5 g 1,2-dichloroethane was added with stirring at 28-30° C. a mixture of 26.7 g aluminum trichloride, 14.8 g acetyl chloride and 75 g 1,2-dichloroethane in the course of one hour and twenty minutes. After an additional stirring period of 30 minutes at 20° C. the mixture was poured on ice and stirred for another hour. The organic layer was washed with subsequently 5%-sodium carbonate solution, saturated sodium chloride solution and concentrated by means of a rotatory evaporator yielding 34.9% 2-acetyl-1,1,3,5-tetramethylindene in 45.6 g residue. Recrystallization from methanol gave 99.4% pure 2-acetyl-1,1,3,5-tetramethylindene.

Workup

  1. additionwas added
  2. stirringAfter an additional stirring period of 30 minutes at 20° C. the mixture
  3. additionwas poured on ice
  4. stirringstirred for another hour
  5. washThe organic layer was washed with subsequently 5%-sodium carbonate solution, saturated sodium chloride solution
  6. concentrationconcentrated by means of a rotatory evaporator

Sources & evidence

ORD record
ord-1f8f4d2895604774a05cbf02a9f8126a
Source dataset
uspto-grants-2003_11
Patent number
US06645932B2

Reaction notes

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