Trimethylsilane → 1-Chloro-4-(1-trimethylsilylhexyl)benzene

HRID 248562

Reaction equation

HRID 248562 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[CH3:14][SiH:15]([CH3:17])[CH3:16]>C1(C)C=CC=CC=1.ClCCl.C1([Pt](Cl)(Cl)C2C=CC=C2)C=CC=C1>[CH3:14][Si:15]([CH3:17])([CH3:16])[CH:1]([C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 2

HCID 70435TrimethylsilaneHCID 116369934-(5-Hexenyl)-1-chlorobenzene

Product 1

HCID 197638591-Chloro-4-(1-trimethylsilylhexyl)benzeneYield 79.8%

Reagents, catalysts & solvents 3

HCID 178479810HCID 178479810, compoundCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

About 15.9 g (0.082 Mol) of 4-(5-hexenyl)-1-chlorobenzene were dissolved in 10 ml of toluene, 0.8 ml of a 1 percent solution of dicyclopentadienylplatinum dichloride in dichloromethane (corresponding to 100 ppm of Pt) were added, and the mixture was introduced into a 100 ml bench autoclave. About 10 g (0.147 Mol) of trimethylsilane in the condensed state were added, the autoclave was sealed, and 5 MPa of nitrogen were injected. The mixture was warmed at 70° to 80° C. for 90 minutes (8 MPa, internal stirring). The mixture was then cooled, the solvent was stripped off, and the resultant residue fractionated. About 17.6 g of 4-(1-trimethylsilylhexyl)-1-chlorobenzene, corresponding to 77.1 percent of theory, were obtained at 0.1 hPa and at a boiling range of 107° to 112° C.

Workup

  1. additionthe mixture was introduced into a 100 ml bench autoclave
  2. customthe autoclave was sealed
  3. temperatureThe mixture was warmed at 70° to 80° C. for 90 minutes
  4. temperatureThe mixture was then cooled

Sources & evidence

ORD record
ord-08f010ad8f0a4985ad42f4c7a35b6ff7
Source dataset
uspto-grants-1993_05
Patent number
US05210247

Linked notes

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