Sodium Hydroxide → 2-Azido-2-methoxyacetic acid

HRID 1658004Notes

Reaction equation

HRID 1658004 reaction equation
[OH-].[Na+].[N:3]([CH:6]([O:11][CH3:12])[C:7]([O:9]C)=[O:8])=[N+:4]=[N-:5]>CO>[N:3]([CH:6]([O:11][CH3:12])[C:7]([OH:9])=[O:8])=[N+:4]=[N-:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20357785Methyl 2-azido-2-methoxyacetate

Product 1

HCID 215299592-Azido-2-methoxyacetic acidYield 93.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous sodium hydroxide (30 ml. of a 2.5 N solution) is added dropwise over 15 minutes to a stirring solution of methyl 2-azido-2-methoxyacetate (10.40 g., 72 mmole) in methanol (8.5 ml.). The mixture becomes warm and cloudy during the addition. The methanol is removed under reduced pressure and the aqueous residue is acidified to pH 1 with concentrated sulfuric acid and extracted with ether. The combined ethereal extracts are dried over sodium sulfate and evaporated in vacuo to leave 2-azido-2-methoxyacetic acid (8.82 g.) as a clear liquid.

Workup

  1. temperatureThe mixture becomes warm and cloudy during the addition
  2. customThe methanol is removed under reduced pressure
  3. extractionextracted with ether
  4. dry with materialThe combined ethereal extracts are dried over sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-44b71b0eef774d209f3f4bd62c86c095
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

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