1,3-Bis[4-(4-nitrophenoxy)butyl]-1,1,3,3-tetramethyldisiloxane → Benzenamine, 4,4'-[(1,1,3,3-tetramethyl-1,3-disiloxanediyl)bis(4,1-butanediyloxy)]bis-

HRID 1963764Notes

Reaction equation

HRID 1963764 reaction equation
[N+:1]([C:4]1[CH:35]=[CH:34][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][Si:13]([CH3:33])([CH3:32])[O:14][Si:15]([CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=2)([CH3:17])[CH3:16])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd]>[NH2:1][C:4]1[CH:35]=[CH:34][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][Si:13]([CH3:33])([CH3:32])[O:14][Si:15]([CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:24]=[CH:25][C:26]([NH2:29])=[CH:27][CH:28]=2)([CH3:16])[CH3:17])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 866652931,3-Bis[4-(4-nitrophenoxy)butyl]-1,1,3,3-tetramethyldisiloxaneHCID 178418361HCID 178418361, compound

Product 1

HCID 20428206Benzenamine, 4,4'-[(1,1,3,3-tetramethyl-1,3-disiloxanediyl)bis(4,1-butanediyloxy)]bis-

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1,3-bis[4-(4-nitrophenoxy)butyl]-1,1,3,3-tetramethyldisiloxane (2a) (1.35 g; 3.38 mmol) and 10 mL of a 10 wt % Pd/C (0.0393 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 (1.18 g, 98% of yield).

Workup

  1. filtrationThe solution was filtrated by Celite
  2. concentrationconcentrated
  3. customto obtain
  4. customa colorless oily material (1.18 g, 98% of yield)

Sources & evidence

ORD record
ord-37f20157c2e540fc9ca1678103886f3d
Source dataset
uspto-grants-2013_04
Patent number
US08415451B2

Reaction notes

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