Water → 1H-Indene, 2,3-dihydro-1,3-dimethyl-1-(2-methyl-2-phenylpropyl)-3-phenyl-

HRID 1585862Notes

Reaction equation

HRID 1585862 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].[Al+3].[Cl-].[Cl-].[Cl-].O>C1(C)C=CC=CC=1>[CH3:3][C:2]1([CH2:3][C:2]([CH3:1])([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH3:1])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:2]([CH3:7])([C:1]2[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 7407Alpha-MethylstyreneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1705851H-Indene, 2,3-dihydro-1,3-dimethyl-1-(2-methyl-2-phenylpropyl)-3-phenyl-Yield 46.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a four-necked 2000 ml-volume flask equipped with a stirring machine, a dropping funnel, a Dimroth condenser and a thermometer, there was added a solution of 300.4 g of α-methylstyrene in 1200 g of toluene, followed by setting the temperature thereof to 0° C. by dipping the flask in ice-water and gradual dropwise addition of 300 ml of a toluene solution containing a catalyst, i.e., 1.02 g AlCl3 -2.5 ml CH3NO3 to the contents of the flask with stirring. The reaction solution at the completion of the reaction-was colored pale yellow. After the completion of the reaction, water was gently dropwise added to the reaction system to thus decompose the catalyst. Then the organic phase was washed with water, dried and concentrated. Further the organic phase was subjected to vacuum distillation under a degree of vacuum of 670 Pa and at a temperature ranging from 218 to 221° C. to give 140.0 g of 1,3-dimethyl-3-phenyl-1-(2-methyl-2-phenylpropyl) indane (MPI).

Workup

  1. customTo a four-necked 2000 ml-volume flask equipped with a stirring machine, a dropping funnel
  2. customto 0° C.
  3. customThe reaction solution at the completion of the reaction-was colored pale yellow
  4. additionwas gently dropwise added to the reaction system
  5. washThen the organic phase was washed with water
  6. customdried
  7. concentrationconcentrated
  8. distillationFurther the organic phase was subjected to vacuum distillation under a degree of vacuum of 670 Pa and at a temperature
  9. customranging from 218 to 221° C.

Sources & evidence

ORD record
ord-1f8b2d481ed744a9bd7d8ab03d791111
Source dataset
uspto-grants-1999_08
Patent number
US05939593

Reaction notes

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