Chlorodimethylsilane → Propenylanisole

HRID 129219

Reaction equation

HRID 129219 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11])[CH:2]=[CH2:3].C[SiH](C)Cl>[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11])=[CH:2][CH3:3]

Participants

4

Reactant 2

HCID 66108ChlorodimethylsilaneHCID 971012-Allylanisole

Product 1

HCID 3014070Propenylanisole

Reagents, catalysts & solvents 1

HCID 61859Chloroplatinic acidCatalyst

Conditions

Temperature
70 °C

Procedure

148 g (1.0 mol) of 2-allylanisole are mixed with 8 mg of hexachloroplatinic acid under a nitrogen atmosphere and heated to 70° C. 114 g (1.2 mol) of dimethylchlorosilane are metered into the mixture over the course of two hours and the mixture is stirred at 70° C. for a further four hours. Excess dimethylchlorosilane is then removed in vacuo and 2-propenylanisole which is formed by isomerization is separated off using a short Vigreux column. 204 g of 3-(2-anisyl)propyldimethylchlorosilane are obtained as a clear liquid having an acid number of 227.

Workup

  1. customare metered into the mixture over the course of two hours
  2. customExcess dimethylchlorosilane is then removed in vacuo

Sources & evidence

ORD record
ord-f172715bb07448328751663f316b5838
Source dataset
uspto-grants-1995_11
Patent number
US05466845

Linked notes

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