HCID 22734917, compound → Ethanol, 2,2′-[(2-amino-1,4-phenylene)bis(oxy)]bis-, 1,1′-diacetate

HRID 491234Notes

Reaction equation

HRID 491234 reaction equation
[N+:1]([C:4]1[C:5]([O:19][CH2:20][CH2:21][O:22][C:23](=[O:25])[CH3:24])([CH:7]=[CH:8][C:9]([O:12][CH2:13][CH2:14][O:15][C:16](=[O:18])[CH3:17])(O)[CH:10]=1)O)([O-])=O.[H][H]>C(O)C.[Pd]>[C:23]([O:22][CH2:21][CH2:20][O:19][C:5]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][CH2:14][O:15][C:16](=[O:18])[CH3:17])=[CH:10][C:4]=1[NH2:1])(=[O:25])[CH3:24]

Participants

5

Reactant 2

HCID 22734917HCID 22734917, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 22708942Ethanol, 2,2′-[(2-amino-1,4-phenylene)bis(oxy)]bis-, 1,1′-diacetateYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Nitro-1,4-bis-(2-acetoxyethoxy)hydroquinone (115 g) was dissolved in ethanol at 50° C. and reduced with hydrogen in the presence of palladium catalyst (2 g, 5% Pd/C). When uptake of hydrogen ceased the solution was screened to remove the catalyst and the filtrates allowed to cool to room temperature. The crystalline solid was isolated by filtration and dried under vacuum to give 90 g of product.

Workup

  1. customto remove the catalyst
  2. customThe crystalline solid was isolated by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-58dcd9e3d7424d9d8935589dd4430a63
Source dataset
uspto-grants-2009_05
Patent number
US07530685B2

Reaction notes

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