Sodium Hydroxide → 2,2-Bis(2-aminoethoxy)propane

HRID 1612902Notes

Reaction equation

HRID 1612902 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][O:8][C:9]([O:12][CH2:13][CH2:14][N:15]2C(=O)C3=CC=CC=C3C2=O)([CH3:11])[CH3:10])C(=O)C2=CC=CC=C12.[OH-].[Na+]>O>[NH2:15][CH2:14][CH2:13][O:12][C:9]([O:8][CH2:7][CH2:6][NH2:5])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 197770212,2-Di-(2-phthalimidoethoxy)propane

Product 1

HCID 197770192,2-Bis(2-aminoethoxy)propaneYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,2-Di-(2-phthalimidoethoxy)propane (46.2 gm, 0.11 mole), sodium hydroxide (43.7 gm, 1.10 mole) and 100 mL of H2O were combined and refluxed for 20 hours. After cooling this solution was extracted with p-dioxane in a liquid-liquid extractor for 20 hours. The p-dioxane was removed by rotary evaporation to give a yellow oil. The oil was distilled under reduced pressure yielding 12.5 gm of a clear colourless oil: 0.077 mole, 71%. bp 107°-110° C./0.18 mm Hg. NMR δ(CDCl3)3.41(tr, 4 H, J=6 Hz, CH2O), 2.78(tr, 4 H, J=6 Hz, NCH2), 1.33 (s, 6 H, geminal (CH3)2), 1.20(s, 4 H, NH2).

Workup

  1. temperaturerefluxed for 20 hours
  2. temperatureAfter cooling this solution
  3. extractionwas extracted with p-dioxane in a liquid-liquid extractor for 20 hours
  4. customThe p-dioxane was removed by rotary evaporation
  5. customto give a yellow oil
  6. distillationThe oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-4242f4a5a98040fa925899278b8f291d
Source dataset
uspto-grants-1993_03
Patent number
US05191015

Reaction notes

Loading…