Allyl chloride → (3-Chloropropyl)triethoxysilane

HRID 52683

Reaction equation

HRID 52683 reaction equation
[CH2:1]([Cl:4])[CH:2]=[CH2:3].[CH2:5]([O:7][SiH:8]([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])[CH3:6]>C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Ir].[Ir].CC1C=CC(C)=CC=1>[Cl:4][CH2:1][CH2:2][CH2:3][Si:8]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])[O:7][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 7850Allyl chlorideHCID 13830Triethoxysilane

Product 1

HCID 78771(3-Chloropropyl)triethoxysilaneYield 61%

Reagents, catalysts & solvents 2

HCID 6436381Chloro(1,5-cyclooctadiene)iridium(I) dimerCatalystHCID 7809P-XyleneSolvent

Procedure

In analogy to Example 3, a homogeneous reaction solution of 4 g of p-xylene, 3.8 g (0.05 mol) of allyl chloride (instead of 4.2 g corresponding to 0.055 mol), 8.2 g (0.05 mol) of triethoxysilane and 0.16 mg (10-3 mol %) of chloro-(1,5-cyclooctadiene)iridium(I) dimer were reacted without a relatively long mixing or storage time. Analysis by gas chromatography gave a product yield of only 61% of 3-chloropropyltriethoxysilane.

Workup

  1. additiona relatively long mixing

Sources & evidence

ORD record
ord-1046655f81d5414dad9edc05ddc70660
Source dataset
uspto-grants-1997_04
Patent number
US05616762

Linked notes

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