4-Aminophenol → 4,4'-Diaminodiphenyl Ether

HRID 1670186Notes

Reaction equation

HRID 1670186 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[OH-].[Na+].[CH3:19]S(C)=O>>[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:8]2[CH:7]=[CH:19][C:5]([NH2:6])=[CH:4][CH:3]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 4

HCID 4034-AminophenolHCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 818524-Chloropyridine hydrochloride

Product 1

HCID 75794,4'-Diaminodiphenyl EtherYield 94%

Conditions

Temperature
100 °C

Procedure

A solution of 4-chloropyridine hydrochloride (Aldrich, 3.0 g, 20.0 mmol) in dimethyl sulfoxide (40 mL) was treated with 4-aminophenol (Aldrich, 2.1 g, 20.0 mmol) and sodium hydroxide pellets (2.0 g, 50.0 mmol) and the mixture was heated at 100° C. for 18 h. The mixture was cooled to room temperature, poured onto a mixture of ice-water (300 g) and extracted with Et2O (3×150 mL). The combined extracts were washed with brine, dried (MgSO4) and concentrated to give the 4-(4-aminophenoxy)aniline as a pale yellow solid (3.5 g, 94%). 1H NMR (DMSO-d6) δ 8.38 (dd, 2H, J=5.5, 1.5 Hz), 6.83-6.79 (m, 4H), 6.63-6.59 (m, 2H), 5.13 (br s, 2H); MS (ESI+) m/z 187.2 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with Et2O (3×150 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fd33db8bf59c415db869e590f8bf7ca7
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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