HCID 86761339, compound → HCID 22321278, compound

HRID 2425337Notes

Reaction equation

HRID 2425337 reaction equation
[N+:1]([C:4]1[CH:40]=[CH:39][C:7]([O:8][C:9]2[CH:38]=[CH:37][C:12]([O:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]4[CH:26]=[CH:25][C:24]([O:27][C:28]5[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][CH:29]=5)=[CH:23][CH:22]=4)=[CH:16][CH:15]=3)=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O>[Pd].C1COCC1>[NH2:34][C:31]1[CH:32]=[CH:33][C:28]([O:27][C:24]2[CH:25]=[CH:26][C:21]([O:20][C:17]3[CH:16]=[CH:15][C:14]([O:13][C:12]4[CH:37]=[CH:38][C:9]([O:8][C:7]5[CH:39]=[CH:40][C:4]([NH2:1])=[CH:5][CH:6]=5)=[CH:10][CH:11]=4)=[CH:19][CH:18]=3)=[CH:22][CH:23]=2)=[CH:29][CH:30]=1

Participants

4

Reactant 1

HCID 86761339HCID 86761339, compound

Product 1

HCID 22321278HCID 22321278, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 150 ml hydrogenation bottle was charged with 11.3 g (0.021 mol) 1,4-bis[4-(4-nitrophenoxy)phenoxy]benzene, 100 ml dry THF, and 0.5 g 10% Pd—C. The bottle was placed in a Parr-hydrogenator and the nitro group was reduced under H2-atmosphere (50 psi) in 5 h. at room temperature. The THF solution was filtered over a short silica-gel/celite patch and the THF was removed by distillation. Pure 1,4-bis[4-(4-aminophenoxy)phenoxy]benzene (P3) was obtained after recrystallization from acetone/water (95/5) as off white crystals. Yield: 8.6 g (86%). Mp: 170° C.; IR(KBr): vmax 3384, 3316, 1499, 1275, 1223, 1193, 1105, 1097, 865, 846, 827 cm−1; 1H-NMR (CDCl3) δ (ppm): 3.55 (s, 4H), 6.64 (d, 4H, J=9 Hz), 6.83 (d, 4H, J=9 Hz), 6.87-6.93 (m, 12H); 13C-NMR (CDCl3) δ (ppm); 116.2. 118.6, 119.5, 119.7, 119.8, 120.5, 142.4, 149.1, 152.2, 153.1, 154.3.

Workup

  1. customin 5 h.
  2. customat room temperature
  3. filtrationThe THF solution was filtered over a short silica-gel/celite patch
  4. customthe THF was removed by distillation

Sources & evidence

ORD record
ord-b45773ea416145e994eb1a5d06b12857
Source dataset
uspto-grants-2011_06
Patent number
US07964698B2

Reaction notes

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