3-Aminophenol → HCID 12666331, compound

HRID 328910Notes

Reaction equation

HRID 328910 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9]([N:13]1[CH2:16][CH:15]([OH:17])[CH2:14]1)([CH3:12])([CH3:11])[CH3:10].[OH-].[K+]>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:16][CH:15]([OH:17])[CH2:14][NH:13][C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 3

HCID 115683-AminophenolHCID 14797Potassium HydroxideHCID 2879861-tert-Butyl-3-hydroxyazetidine

Product 1

HCID 12666331HCID 12666331, compoundYield 42.3%

Conditions

Temperature
140 °C

Procedure

A mixture of 21.8 parts of m-aminophenol, 22 parts of 1-(tert.-butyl)-3-azetidinol and 0.7 part of potassium hydroxide was heated under nitrogen gas at 140° C. for 8 hours with agitation. The reaction mixture was cooled and treated in the same manner as in Example 39. Recrystallization from benzene gave 17.2 parts of 1-(3'-aminophenoxy)-3-(tert.-butylamino)-2-propanol in the form of colorless needles melting at 105° - 106° C. The yield was 42.3%. The results of infra-red spectrum analysis are as follows:

Workup

  1. temperatureThe reaction mixture was cooled
  2. additiontreated in the same manner as in Example 39
  3. customRecrystallization from benzene

Sources & evidence

ORD record
ord-39254cdb8cc8457fbe9229262b30fef5
Source dataset
uspto-grants-1977_04
Patent number
US04018824

Reaction notes

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