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

HRID 1963758Notes

Reaction equation

HRID 1963758 reaction equation
[N+:1]([C:4]1[CH:43]=[CH:42][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][Si:13]([CH3:41])([CH3:40])[O:14][Si:15]([CH3:39])([CH3:38])[O:16][Si:17]([CH3:37])([CH3:36])[O:18][Si:19]([CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][CH:28]=2)([CH3:21])[CH3:20])=[CH:6][CH:5]=1)([O-])=O.[H][H]>>[NH2:1][C:4]1[CH:43]=[CH:42][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][Si:13]([CH3:40])([CH3:41])[O:14][Si:15]([CH3:39])([CH3:38])[O:16][Si:17]([CH3:37])([CH3:36])[O:18][Si:19]([CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]2[CH:28]=[CH:29][C:30]([NH2:33])=[CH:31][CH:32]=2)([CH3:20])[CH3:21])=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 866652921,7-Bis(4-nitrophenoxybutyl)-1,1,3,3,5,5,7,7-octamethyltetrasiloxaneHCID 178418361HCID 178418361, compound

Product 1

HCID 687491381,7-Bis(4-aminophenoxybutyl)-1,1,3,3,5,5,7,7-octamethyltetrasiloxaneYield 99.6%

Procedure

2.26 g of the above 2b (3.38 mmol) and 15 mL of a 10 wt % Pd/C ethyl acetate solution (0.0209 g) 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 1,7-bis(4-aminophenoxybutyl)-1,1,3,3,5,5,7,7-octamethyltetrasiloxane (3c) (2.05 g, 99% of yield) represented by the following formula. Various measurements were carried out with regard to the obtained 1,7-bis(4-aminophenoxybutyl)-1,1,3,3,5,5,7,7-octamethyltetrasiloxane (3c), and results are shown below.

Workup

  1. filtrationThe solution was filtrated by Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f2efc751043d4e94a990b0486a8b5bff
Source dataset
uspto-grants-2013_04
Patent number
US08415451B2

Reaction notes

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