Ethanol → Diethyl iminodiacetate

HRID 703258Notes

Reaction equation

HRID 703258 reaction equation
[NH:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4].B(F)(F)F.[CH3:14][CH2:15]OCC.[CH2:19](O)[CH3:20]>>[NH:1]([CH2:6][C:7]([O:9][CH2:19][CH3:20])=[O:8])[CH2:2][C:3]([O:5][CH2:14][CH3:15])=[O:4]

Participants

4

Reactant 3

HCID 702EthanolHCID 8000Boron trifluoride etherateHCID 8897Iminodiacetic acid

Product 1

HCID 80502Diethyl iminodiacetateYield 92%

Procedure

To a magnetically stirred suspension of iminodiacetic acid (50 g, 0.376 mol) in absolute ethanol (1000 ml) under N2 was added boron trifluoride etherate (100 g, 1.127 mmol). The reaction mixture was refluxed for 3 days and concentrated in vacuo to a volume of 150 ml. A saturated NH4Cl solution (500 ml) was added and the reaction mixture was extracted with CH2Cl2 (3×250 ml). The combined organic layers were dried and concentrated in vacuo. The crude product was distilled at 10 mm Hg to give 65.2 g (92% yield) of iminodiacetic acid, diethyl ester as a colorless liquid.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 days
  2. concentrationconcentrated in vacuo to a volume of 150 ml
  3. additionA saturated NH4Cl solution (500 ml) was added
  4. extractionthe reaction mixture was extracted with CH2Cl2 (3×250 ml)
  5. customThe combined organic layers were dried
  6. concentrationconcentrated in vacuo
  7. distillationThe crude product was distilled at 10 mm Hg

Sources & evidence

ORD record
ord-39d04681b8bb497a977de382d46967f5
Source dataset
uspto-grants-1991_01
Patent number
US04981985

Reaction notes

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