O-Xylene → 1,7-Bis(4-nitrophenoxybutyl)-1,1,3,3,5,5,7,7-octamethyltetrasiloxane

HRID 1963757Notes

Reaction equation

HRID 1963757 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4].[CH3:15][SiH:16]([CH3:29])[O:17][Si:18]([CH3:28])([CH3:27])[O:19][Si:20]([CH3:26])([CH3:25])[O:21][SiH:22]([CH3:24])[CH3:23].[C:30]1(C)[C:31](C)=[CH:32][CH:33]=[CH:34][CH:35]=1>C1(C)C=CC=CC=1>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH2:4][Si:22]([CH3:23])([CH3:24])[O:21][Si:20]([CH3:25])([CH3:26])[O:19][Si:18]([CH3:27])([CH3:28])[O:17][Si:16]([CH2:4][CH2:3][CH2:2][CH2:1][O:5][C:34]2[CH:33]=[CH:32][C:31]([N+:12]([O-:14])=[O:13])=[CH:30][CH:35]=2)([CH3:29])[CH3:15])=[CH:7][CH:8]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 70465Dimethylsilyloxy-[dimethylsilyloxy(dimethyl)silyl]oxy-dimethylsilaneHCID 112177694-(3-Butenyloxy)nitrobenzene

Product 1

HCID 866652921,7-Bis(4-nitrophenoxybutyl)-1,1,3,3,5,5,7,7-octamethyltetrasiloxaneYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the above 4-(3-butenyloxy)nitrobenzene (1) (4.27 g; 22.1 mmol), 1,1,3,3,5,5,7,7-octamethyltetrasiloxane (2.97 g; 9.98 mmol) dissolved in 20 mL of toluene and Karsted catalyst (0.25 mL; a 2% xylene solution of platinum divinyl tetramethyldisiloxane complex) were added. The reaction solution was heated to reflux for 21 hours in a nitrogen atmosphere, and then subjected to a reduced pressure to remove toluene. The obtained materials were purified by column chromatography to obtain a light yellow oily material of 1,7-bis(4-nitrophenoxybutyl)-1,1,3,3,5,5,7,7-octamethyltetrasiloxane (2b) (5 g, 75% of yield) represented by the following formula.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux for 21 hours in a nitrogen atmosphere
  3. customto remove toluene
  4. customThe obtained materials were purified by column chromatography

Sources & evidence

ORD record
ord-4780a9db2704429994ee47d2d1819ab2
Source dataset
uspto-grants-2013_04
Patent number
US08415451B2

Reaction notes

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