4-Aminophenol → 4-(2,5-Dimethyl-1H-pyrrol-1-yl)phenol

HRID 2371960Notes

Reaction equation

HRID 2371960 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.[CH2:9]([CH2:13][C:14](=O)[CH3:15])[C:10]([CH3:12])=O.O>C1(C)C=CC=CC=1>[CH3:15][C:14]1[N:7]([C:6]2[CH:5]=[CH:4][C:3]([OH:8])=[CH:2][CH:1]=2)[C:10]([CH3:12])=[CH:9][CH:13]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 962WaterHCID 80352,5-Hexanedione

Product 1

HCID 12833534-(2,5-Dimethyl-1H-pyrrol-1-yl)phenol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4.0 g of p-aminophenol and 4.0 g of acetonylacetone is heated under reflux in toluene for 3 hours using a Dean Stark water separator to yield 4-(2,5-dimethyl-1H-pyrrol-1-yl)-phenol. Condensation with ethyl alpha-bromoisobutyrate in ethyl alcohol in the presence of potassium carbonate gives ethyl 2-[4-(2,5-di-methyl-1H-pyrrol-1-yl)-phenoxy]-2-methylpropanoate. Hydrolysis with 1.5 N sodium hydroxide solution yields 2-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-phenoxy]-2-methyl-propanoic acid, m.p. 178°-180°.

Workup

  1. temperatureis heated

Sources & evidence

ORD record
ord-1555db990954452fad2831faa27314c6
Source dataset
uspto-grants-1992_03
Patent number
US05096919

Reaction notes

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