4-Aminophenol → 4-[3-(t-Butylamino)-2-hydroxypropoxy]aniline

HRID 2198857Notes

Reaction equation

HRID 2198857 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.[C:9]([N:13]1[CH2:16][CH:15]([OH:17])[CH2:14]1)([CH3:12])([CH3:11])[CH3:10].[OH-].[K+]>Cl>[NH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:8][CH2:16][CH:15]([OH:17])[CH2:14][NH:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:2][CH:1]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 14797Potassium HydroxideHCID 2879861-tert-Butyl-3-hydroxyazetidine

Product 1

HCID 126663354-[3-(t-Butylamino)-2-hydroxypropoxy]anilineYield 19.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 21.8 g of p-aminophenol, 22 g of 1-(tert.-butyl)-3-azetidinol and 0.73 g of potassium hydroxide was heated under nitrogen gas at 140° C. for 8 hours with agitation. The reaction mixture was cooled and dissolved in concentrated hydrochloric acid and the solution was extracted with ether. The hydrochloric acid aqueous solution was made alkaline with 10% -NaOH aqueous solution and then extracted with ether. The ether solution was washed with water and dried over anhydrous sodium sulfate. Then ether was distilled off and the residue was recrystallized from benzene. as a result, 8 g of 1-(p-aminophenoxy)-3-(tert.-butylamino)-2-propanol melting at 125°-127° C. were obtained. The results of infra-red spectrum analysis and nuclear magnetic resonance analysis are as follows:

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe solution was extracted with ether
  3. extractionextracted with ether
  4. washThe ether solution was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThen ether was distilled off
  7. customthe residue was recrystallized from benzene

Sources & evidence

ORD record
ord-1221b23b0b7340f7a68015f8ddd6ee00
Source dataset
uspto-grants-1982_11
Patent number
US04360464

Reaction notes

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