Water → 4-azidobutanoic Acid

HRID 396685Notes

Reaction equation

HRID 396685 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]([O:9]CC)=[O:8])=[N+:2]=[N-:3].[OH-].[K+].O>CO>[N:1]([CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 12382175Ethyl 4-azidobutanoate

Product 1

HCID 118047834-azidobutanoic AcidYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 4-azidobutyrate (8.06 g, 51.3 mmol) and KOH (14.4 g, 0.256 mol) were dissolved into a mixture of 100 ml of water and 120 ml of MeOH. The solution was stirred at 0° C. for 2 hrs and then MeOH was removed in vacuo. The aqueous layer was extracted by CHCl3 (50 ml), acidified to pH=1 by 2N aqueous HCl and extracted by Et2O (2×100 ml). The organic layers were combined, washed with water (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 4-azidobutyric acid (5.30 g, 80%) was obtained as a colorless oil.

Workup

  1. customMeOH was removed in vacuo
  2. extractionThe aqueous layer was extracted by CHCl3 (50 ml)
  3. extractionextracted by Et2O (2×100 ml)
  4. washwashed with water (100 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and evaporation of solvent

Sources & evidence

ORD record
ord-71e74ec3863c41b39e8058494ff3056a
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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