Dichloromethane → HCID 20085079, compound

HRID 2225355Notes

Reaction equation

HRID 2225355 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 (1.0L, dried over 3Å molecular sieves) in 4L beaker, in a drybox at room temperature. After the addition of 1L AMS, about 0.2L 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 0.3L 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.11 H) 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.11 H) 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-fc0f18aea89b46848bb9aec26be76f68
Source dataset
uspto-grants-1994_09
Patent number
US05344592

Reaction notes

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