Water → 2-Propanamine, 1-(3-methylphenoxy)-

HRID 1288233Notes

Reaction equation

HRID 1288233 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[O:5][CH2:6][C:7](=[N:9]O)[CH3:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[O:5][CH2:6][CH:7]([NH2:9])[CH3:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 85437759HCID 85437759, compound

Product 1

HCID 122988962-Propanamine, 1-(3-methylphenoxy)-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1-(3-methylphenoxy)propan-2-one oxime (13.7 g.) in dry ether (100 ml.) was added dropwise, over 45 minutes, to a stirred, refluxing mixture of lithium aluminium hydride (5.85 g.) in dry ether (200 ml.). Stirring and heating were continued for 4 hours and the mixture was cooled and treated cautiously with water (5.8 ml.) followed by 15% aqueous sodium hydroxide (5.8 ml.), and finally, water (17.5 ml.). The mixture was stirred for 30 minutes and then filtered. The filtrate was dried over anhydrous potassium carbonate and evaporated. The residue was distilled to give 1-(3-methylphenoxy)prop-2-ylamine, b.p. 124°-128°/13 mm.

Workup

  1. temperaturerefluxing
  2. temperatureheating
  3. temperaturethe mixture was cooled
  4. stirringThe mixture was stirred for 30 minutes
  5. filtrationfiltered
  6. dry with materialThe filtrate was dried over anhydrous potassium carbonate
  7. customevaporated
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-ab449766ab784b499fd2ecb646f60432
Source dataset
uspto-grants-1976_10
Patent number
US03987158

Reaction notes

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