4-Aminophenol → Phenolindophenol

HRID 1606693

Reaction equation

HRID 1606693 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.N[C:10]1[CH:11]=[CH:12][C:13](C)=[C:14]([OH:16])[CH:15]=1>[OH-].[Na+]>[CH:7]1[C:2](=[N:1][C:11]2[CH:10]=[CH:15][C:14]([OH:16])=[CH:13][CH:12]=2)[CH:3]=[CH:4][C:5](=[O:8])[CH:6]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 178185-Amino-2-methylphenol

Product 1

HCID 10379PhenolindophenolYield 60.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

0.01 mole (1.09 g) of paraaminophenol is dissolved in 100 cm3 of a 0.1 N NaOH solution. A second solution of 0.01 mole (1.23 g) of 5-amino-2-methyl phenol in 100 cm3 of a 0.1N NaOH solution is also prepared. The two solutions are then mixed and air is bubbled in the resulting mixture for about 5 hours at ambient temperature. The reaction medium is then acidified with sufficient HCl to pH 5 to produce 1.2 g of said indophenol which is then filtered off and which, after recrystallization from a dimethylformamide-water mixture, melts at 215°.

Workup

  1. additionThe two solutions are then mixed
  2. customair is bubbled in the resulting mixture for about 5 hours at ambient temperature

Sources & evidence

ORD record
ord-c37537883b414163b57e733cf95dbcb6
Source dataset
uspto-grants-1976_04
Patent number
US03953508

Linked notes

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