Sodium Hydroxide → 3-[2-Azido-2-(2-hydroxyethoxy)ethoxy]benzoic acid

HRID 1923446Notes

Reaction equation

HRID 1923446 reaction equation
C([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH:13]([N:18]=[N+:19]=[N-:20])[O:14][CH2:15][CH2:16][OH:17])[CH:6]=1)C.[OH-].[Na+]>C(O)C>[N:18]([CH:13]([O:14][CH2:15][CH2:16][OH:17])[CH2:12][O:11][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([OH:21])=[O:3])=[N+:19]=[N-:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 597717683-[2-Azido-2-(2-hydroxyethoxy)ethoxy]benzoic acid ethyl ester

Product 1

HCID 597717663-[2-Azido-2-(2-hydroxyethoxy)ethoxy]benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-[2-Azido-2-(2-hydroxyethoxy)ethoxy]benzoic acid ethyl ester (1.34 g, 4.55 mmol) was stirred with 4 M aqueous sodium hydroxide (11.4 ml, 45.5 mmol) and ethanol (11.4 ml) at room temperature. After 3 hrs, all the solvents were removed under reduced pressure and the residue was dissolved in 50 ml water. The solution was acidified with 1N HCl to pH 2 and then extracted with DCM (3×50 ml). All the DCM extracts were combined, dried over MgSO4 and evaporated under reduced pressure. The title compound was obtained as a colourless solid (1.2 g, 98.7%). ES-MS, m/z 265.85 (M−1).

Workup

  1. customall the solvents were removed under reduced pressure
  2. dissolutionthe residue was dissolved in 50 ml water
  3. extractionextracted with DCM (3×50 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ae720be705a54789adc823f64b21029d
Source dataset
uspto-grants-2012_05
Patent number
US08178360B2

Reaction notes

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