Dichloromethane → HCID 20085079, compound

HRID 1608743Notes

Reaction equation

HRID 1608743 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-].Cl[CH2:15]Cl>>[CH2:15]1[C:5]2[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:2][CH2:3]1.[CH3:3][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:1]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 7407Alpha-Methylstyrene2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 20085079HCID 20085079, compound

Procedure

Alpha-methylstyrene (AMS) (2.0 L, 15.4 mole) was added slowly with stirring over 2 to 3 hrs to a mixture of AlCl3 (0.7 g, 5.2 mole) and dichloromethane (1.0 L, dried over 3 Å molecular sieves) in 4 L beaker, in a drybox at room temperature. After the addition of 1 L AMS, about 0.2 L dichloromethane was added to make up for the solvent evaporated due to the reaction exotherm. After the addition of all AMS, the reaction mixture was deactivated with 0.3 L methanol, washed three times with water, dried over calcium chloride, filtered and volatiles stripped first using a rotary evaporator and then high vacuum. Yield was 1,685 g (93%) of colorless, transparent oil. The material was analyzed to contain 60.5% dimer; 1,1,3-trimethyl-3-phenylindan (Registry No. 3910-35-8; GC/MS: Calc. 236.726, Found 236.157); and 39.5% trimer isomers; 1,3-dimethyl-1-(2-methyl-2-phenylpropyl)-3-phenylindan (Registry No. 41906-7-2; GC/MS: Calc. 354.905, Found 354.234). 1H NMR (CDCl3): ppm 0.8-2.7 (m, br, aliph. 13H), 7.0-7.3 (m, br, arom.11H) The viscosity of the mixture of compounds at 26° C. was 782 cp and was adjusted to 880 cp by distilling off 57 g dimer on a Kugelrohr. When the mixture was distilled, the composition of the distillate was 56.4% dimer and 41.8% trimer.

Workup

  1. additionwas added
  2. customevaporated due to the reaction exotherm
  3. additionAfter the addition of all AMS
  4. washwashed three times with water
  5. dry with materialdried over calcium chloride
  6. filtrationfiltered
  7. customa rotary evaporator
  8. addition1H NMR (CDCl3): ppm 0.8-2.7 (m, br, aliph. 13H), 7.0-7.3 (m, br, arom.11H) The viscosity of the mixture of compounds at 26° C.
  9. distillationby distilling off 57 g dimer on a Kugelrohr
  10. distillationWhen the mixture was distilled

Sources & evidence

ORD record
ord-8d9b59dd8acd40e381a0977e367eb522
Source dataset
uspto-grants-1995_03
Patent number
US05397383

Reaction notes

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