Allyl chloride → Bis{(3-chloropropyl)dichlorosilyl]methane

HRID 260551Notes

Reaction equation

HRID 260551 reaction equation
[Cl:1][SiH:2]([CH2:4][SiH:5]([Cl:7])[Cl:6])[Cl:3].[CH2:8]([Cl:11])[CH:9]=[CH2:10]>C(O)(C)C.[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[Cl:11][CH2:8][CH2:9][CH2:10][Si:2]([CH2:4][Si:5]([Cl:7])([Cl:6])[CH2:10][CH2:9][CH2:8][Cl:11])([Cl:3])[Cl:1]

Participants

5

Reactant 2

HCID 7850Allyl chlorideHCID 57370748Bisdichlorosilylmethane2×

Product 1

HCID 22401806Bis{(3-chloropropyl)dichlorosilyl]methaneYield 35.6%

Reagents, catalysts & solvents 2

HCID 61859Chloroplatinic acidCatalystHCID 3776IsopropanolSolvent

Procedure

To a 100 ml, three neck, round bottomed flask equipped with a dropping funnel and a reflux condenser, 6 g(0.03 mole) of bisdichlorosilylmethane, 6.5 g(0.08 mole) of allyl chloride, and 60 μl of 1% chloroplatinic acid solution in isopropanol, at reflux using a 80° C. oil bath for 3 hours under the dry nitrogen atmosphere. Gas chromatography analysis showed that no bisdichlorosilylmethane was left. Vacuum distillation of the reaction products gave 3.85 g(110°-112° C./0.05 mmHg) of bis{(3-chloropropyl)dichlorosilyl]methane in 35.6% yield. Besides this product, 4.10 g of (trichlorosilyl){(3-chloropropyl)silyl}methane was also obtained in 38.0% yield and (propyldichlorosilyl){(3-chloropropyl)dichlorosilyl}methane.

Workup

  1. customTo a 100 ml, three neck, round bottomed flask equipped with a dropping funnel and a reflux condenser
  2. customusing a 80° C.
  3. customfor 3 hours
  4. waitwas left
  5. distillationVacuum distillation of the reaction products

Sources & evidence

ORD record
ord-415a0565364e4d0c9aae56d708bae72b
Source dataset
uspto-grants-1996_06
Patent number
US05527934

Reaction notes

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