1,11-Bis[4-(4-nitrophenoxy)butyl]-1,1,3,3,5,5,7,7,9,9,11,11-dodecamethylhexasiloxane → HCID 68750974, compound

HRID 1963772Notes

Reaction equation

HRID 1963772 reaction equation
[N+:1]([C:4]1[CH:51]=[CH:50][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][Si:13]([CH3:49])([CH3:48])[O:14][Si:15]([CH3:47])([CH3:46])[O:16][Si:17]([CH3:45])([CH3:44])[O:18][Si:19]([CH3:43])([CH3:42])[O:20][Si:21]([CH3:41])([CH3:40])[O:22][Si:23]([CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-])=O)=[CH:33][CH:32]=2)([CH3:25])[CH3:24])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd]>[NH2:1][C:4]1[CH:51]=[CH:50][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][Si:13]([CH3:48])([CH3:49])[O:14][Si:15]([CH3:47])([CH3:46])[O:16][Si:17]([CH3:45])([CH3:44])[O:18][Si:19]([CH3:43])([CH3:42])[O:20][Si:21]([CH3:41])([CH3:40])[O:22][Si:23]([CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:32]=[CH:33][C:34]([NH2:37])=[CH:35][CH:36]=2)([CH3:24])[CH3:25])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 866653001,11-Bis[4-(4-nitrophenoxy)butyl]-1,1,3,3,5,5,7,7,9,9,11,11-dodecamethylhexasiloxaneHCID 178418361HCID 178418361, compound

Product 1

HCID 68750974HCID 68750974, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1.02 g of the above (2A) (1.25 mmol) and 10 mL of a 10 wt % Pd/C (0.0203 g) ethyl acetate solution were mixed, and stirred for 2 days in a hydrogen atmosphere at room temperature. The solution was filtrated by Celite and then concentrated to obtain a colorless oily material of 1,11-bis[4-(4-aminophenoxy)butyl]-1,1,3,3,5,5,7,7,9,9,11,11-dodecamethylhexasiloxane (3A) (0.943 g, 99% of yield) represented by the following formula. Various measurements were carried out with regard to the obtained (3A), and results are shown below.

Workup

  1. filtrationThe solution was filtrated by Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d01881a5505a4490a501ad912b1d5719
Source dataset
uspto-grants-2013_04
Patent number
US08415451B2

Reaction notes

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