Water → 6-azidohexanoic Acid

HRID 322194Notes

Reaction equation

HRID 322194 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11]CC)=[O:10])=[N+:2]=[N-:3].[OH-].[K+].O>CO>[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 12382177HCID 12382177, compound

Product 1

HCID 110409496-azidohexanoic AcidYield 93.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 6-azidohexanoate (8.59 g, 44.8 mmol) and KOH (13.0 g, 0.231 mol) were dissolved into a mixture of 120 ml of water and 180 ml of MeOH. The solution was stirred at 0° C. for 2 hrs then MeOH was removed in vacuo. The aqueous layer was extracted by CHCl3 (2×100 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, 6-azidohexanoic acid (6.56 g, 93%) was obtained as a colorless oil.

Workup

  1. customMeOH was removed in vacuo
  2. extractionThe aqueous layer was extracted by CHCl3 (2×100 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-500a20c669a64238b38fbbe56b598929
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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