Cyclohexene → Cyclohexylphenethyldichlorosilane

HRID 848829Notes

Reaction equation

HRID 848829 reaction equation
[CH2:1]([SiH:9]([Cl:11])[Cl:10])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1>C(O)(C)C.[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[CH:12]1([Si:9]([CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)([Cl:11])[Cl:10])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 123907249Monophenethyldichlorosilane

Product 1

HCID 54253331CyclohexylphenethyldichlorosilaneYield 60.7%

Reagents, catalysts & solvents 2

HCID 61859Chloroplatinic acidCatalystHCID 3776IsopropanolSolvent

Procedure

Then into a 100 ml pressure-proof stainless steel reactor; 6.21 g (30.3 millimol) of the above-mentioned phenethyldichlorosilane, 4.47 g (54.4 millimol) of cylcohexene and 0.1 ml of a chloroplatinic acid solution in isopropanol (0.03 mol % relative to phenethyldichlorosilane) were charged and sealed. Reaction was carried out in an oil bath at 100° C. with stirring for 17.5 hours. After completion of reaction, the reacted solution was subjected to vacuum distillation to obtain 5.30 g (18.4 millimol) of cyclohexylphenethyldichlorosilane. This cyclohexylphenethyldichlorosilane had a boiling point of 112.8°~115.4° C./2.0 mmHg. The infrared spectrum of this compound is shown in FIG. 4. There is no characteristic absorption of Si-H at 2100 cm-1. The NMR spectrum is shown in FIG. 9. There are signals of δ value at 1.0~2.0 ppm (Si--CH2 and C--CH2 --); 2.4~3.0 ppm (--CH2 --C6H5) and 7.15 ppm (--C6H 5). The integral ratio thereof was 14:2:5. In the mass spectrum analysis, parent ion was M+ 286.

Workup

  1. customsealed
  2. customReaction
  3. customwas carried out in an oil bath at 100° C.
  4. customAfter completion of reaction
  5. distillationthe reacted solution was subjected to vacuum distillation

Sources & evidence

ORD record
ord-a1f0695eff4a42e5bad5663368b19f22
Source dataset
uspto-grants-1981_10
Patent number
US04297499

Reaction notes

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