O-Xylene → HCID 21439246, compound

HRID 341329Notes

Reaction equation

HRID 341329 reaction equation
[CH2:1]([O:3][SiH:4]([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])[CH3:2].[CH:11]([CH:13]1[CH2:18][CH2:17][CH:16](C=C)[CH2:15][CH:14]1[CH:21]=[CH2:22])=[CH2:12].CO[SiH](OC)OC.[C:30]1([CH3:37])[C:31](C)=[CH:32][CH:33]=[CH:34][CH:35]=1>[Pt]>[CH2:1]([O:3][Si:4]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])[CH2:22][CH2:21][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][C:13]1([CH:11]=[CH2:12])[CH:30]=[CH2:35])[CH3:2].[CH2:1]([O:3][Si:4]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])[CH2:12][CH2:11][CH:13]=[CH:37][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)[CH3:2].[CH2:1]([O:3][Si:4]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])[CH2:12][CH2:11][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH3:2]

Participants

8

Reactant 4

HCID 7237O-XyleneHCID 13830Triethoxysilane2×HCID 17215TrimethoxysilaneHCID 96529Cyclohexane, 1,2,4-triethenyl-2×

Product 3

HCID 21439246HCID 21439246, compoundHCID 66694494HCID 66694494, compoundHCID 69670692HCID 69670692, compound

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Conditions

Temperature
90 °C

Procedure

(2-Triethoxysilylethyl)divinylcyclohexane was prepared from triethoxysilane and 1,2,4-trivinylcyclohexane using the procedure disclosed in Example 1 of U.S. Pat. No. 7,696,269 for trimethoxysilane and 1,2,4-trivinylcyclohexane. A 5 liter, three-neck round bottomed flask fitted with a heating mantle, mechanical stirrer, addition funnel, Friedrich condenser, nitrogen inlet and thermocouple/temperature controller was charged with 1800 g TVCH (11.1 moles) and 3.6 g of a solution (1 wt % Pt) of Karstedt's platinum catalyst in xylene. The contents of the flask were stirred and heated to 90° C. Triethoxysilane (1641 g, 9.99 moles), which had been placed in the addition funnel, was then added slowly over a four hour period to control the exotherm. The temperature remained between 101-109° C. during the addition. The SiH/Vinyl molar ratio in the reaction was 1:3. GC analysis of the crude reaction product gave 21 wt % unreacted TVCH, 48 wt % mono-hydrosilylated product, ((2-Triethoxysilylethyl)divinylcyclohexane), 26.3 wt % bis ((2-Triethoxysilylethyl)vinylcyclohexane and 2.7 wt % tris ((2-Triethoxysilylethyl)cyclohexane. The gravimetric ratio of mono to bis was 1.82.

Workup

  1. customA 5 liter, three-neck round bottomed flask fitted with a heating mantle, mechanical stirrer, addition funnel, Friedrich condenser, nitrogen inlet
  2. additionwas then added slowly over a four hour period
  3. additionThe temperature remained between 101-109° C. during the addition
  4. customGC analysis of the crude reaction product

Sources & evidence

ORD record
ord-77533884fd6b4a2590e286bc0fe87273
Source dataset
uspto-grants-2014_11
Patent number
US08895770B2

Reaction notes

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