Sodium Hydroxide → 1-(p-Phenoxyphenoxy)-3-(iso-propylamino)-2-propanol

HRID 328889

Reaction equation

HRID 328889 reaction equation
[CH:1]([N:4]1[CH2:7][CH:6]([OH:8])[CH2:5]1)([CH3:3])[CH3:2].[O:9]([C:16]1(O)[CH:21]=[CH:20][CH:19]=[CH:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-:23].[Na+]>>[O:9]([C:16]1[CH:21]=[CH:20][C:19]([O:23][CH2:5][CH:6]([OH:8])[CH2:7][NH:4][CH:1]([CH3:2])[CH3:3])=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 5446771-(Propan-2-yl)azetidin-3-olHCID 205173521-Phenoxyphenol

Product 1

HCID 205173151-(p-Phenoxyphenoxy)-3-(iso-propylamino)-2-propanolYield 58%

Conditions

Temperature
160 °C

Procedure

To a mixture of 5.8 parts of 1-(iso-propyl)-3-azetidinol and 9.3 parts of 1-phenoxyphenol 0.1 part of sodium hydroxide was added, and the mixture was heated under nitrogen gas at 160° C. for 18 hours. The reaction mixture was cooled and extracted with ether. The extract was washed in water and then the solvent was distilled off. Recrystallization of the residue gave 16.1 parts of 1-(p-phenoxyphenoxy)-3-(iso-propylamino)-2-propanol having a melting point of 72°-74° C. The yield was 58%.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ether
  4. washThe extract was washed in water
  5. distillationthe solvent was distilled off
  6. customRecrystallization of the residue

Sources & evidence

ORD record
ord-439dc4399852448982e7db8374c60e24
Source dataset
uspto-grants-1977_04
Patent number
US04018824

Linked notes

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