Ethanol → 1,3,5-tris(4-aminophenoxy)benzene (TAPOB)

HRID 418974Notes

Reaction equation

HRID 418974 reaction equation
[N+:1]([C:4]1[CH:36]=[CH:35][C:7]([O:8][C:9]2[CH:14]=[C:13]([O:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[CH:12]=[C:11]([O:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][CH:27]=3)[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.C(O)C.[H][H]>[Pd].C1COCC1>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:13]2[CH:12]=[C:11]([O:25][C:26]3[CH:27]=[CH:28][C:29]([NH2:32])=[CH:30][CH:31]=3)[CH:10]=[C:9]([O:8][C:7]3[CH:35]=[CH:36][C:4]([NH2:1])=[CH:5][CH:6]=3)[CH:14]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 211850501,1',1''-[Benzene-1,3,5-triyltris(oxy)]tris(4-nitrobenzene)HCID 178418361HCID 178418361, compound2×

Product 1

HCID 211850491,3,5-tris(4-aminophenoxy)benzene (TAPOB)Yield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a 300-mL, 4-necked flask were added 2.46 g (5.03 mmol) of 1,3,5-tri(4-nitrophenoxy)benzene and 5% Pd/C (149 mg), and the inside was replaced with argon. Ethanol (50 mL) and THF (50 mL) were added thereto, and then the flask was equipped with a hydrogen balloon, and the mixture was stirred in a normal-pressure hydrogen atmosphere at room temperature for 3 days. The catalyst was separated by filtration and then the solvent was removed away in vacuo, whereby a desired product was obtained (Quantity: 2.01 g, 5.03 mmol, Yield: 100%).

Workup

  1. customThe catalyst was separated by filtration
  2. customthe solvent was removed away in vacuo, whereby a desired product
  3. customwas obtained (Quantity: 2.01 g, 5.03 mmol, Yield: 100%)

Sources & evidence

ORD record
ord-d7ad10f720884ec180fe5defafbb2ed4
Source dataset
uspto-grants-2012_01
Patent number
US08093349B2

Reaction notes

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