Allyl chloride → Dichloro(3-chloropropyl)(prop-2-en-1-yl)silane

HRID 37598

Reaction equation

HRID 37598 reaction equation
[CH2:1]([Cl:4])[CH:2]=[CH2:3].[CH2:5]([SiH:8]([Cl:10])[Cl:9])[CH:6]=[CH2:7]>>[Cl:9][Si:8]([Cl:10])([CH2:3][CH2:2][CH2:1][Cl:4])[CH2:5][CH:6]=[CH2:7]

Participants

3

Reactant 2

HCID 7850Allyl chlorideHCID 77536Dichloro(prop-2-enyl)silane

Product 1

HCID 22910392Dichloro(3-chloropropyl)(prop-2-en-1-yl)silaneYield 62.5%

Procedure

To a 100 ml, three neck, round bottomed flask equipped with a mechanical stirrer, a dropping funnel, and a condenser were added under the dried nitrogen atmosphere, 542 g (7.08 mol) of allyl chloride and 600 μl of 1% chloroplatinie acid catalyst. Through the dropping funnel was added dropwise 100 g (0.71 mol) of allyldichlorosilane for 30 min while refluxing. After confirming by gas chromatography to complete the reaction, the product was fractionally distilled under vacuum (60°-64° C./0.5 torr) to give 95 g (62.5 % ) of 4,4,7-trichloro-4-sila-1-heptene. Allyltrichlorosilane 30.0 g (19.7 % ) was also obtained as a by-product.

Workup

  1. customTo a 100 ml, three neck, round bottomed flask equipped with a mechanical stirrer, a dropping funnel, and a condenser
  2. temperaturewhile refluxing
  3. customthe reaction
  4. distillationthe product was fractionally distilled under vacuum (60°-64° C./0.5 torr)

Sources & evidence

ORD record
ord-2230f97f6114422fa5f61a53373dbbd8
Source dataset
uspto-grants-1995_05
Patent number
US05420323

Linked notes

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