Sodium Hydroxide → Bis(4-methylphenyl)azidoacetic acid

HRID 2304574Notes

Reaction equation

HRID 2304574 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)([N:13]=[N+:14]=[N-:15])[C:9]([O:11]C)=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)([N:13]=[N+:14]=[N-:15])[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18435794Methyl bis(4-methylphenyl)azidoacetate

Product 1

HCID 18435787Bis(4-methylphenyl)azidoacetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl bis(4-methylphenyl)azidoacetate (2.07 g, 7.01 mmol) in tetrahydrofuran(15 mL) was added 2 M aqueous sodium hydroxide (3.86 ml, 7.71 mmol). The mixture was stirred at room temperature for 18 hours, and then the solvents were removed in vacuo. The residue was dissolved in ethyl acetate and washed with 1M HCl and brine. The organic layer was dried over sodium sulfate, filtered and concentrated to give the title compound as a waxy solid which was used as is.

Workup

  1. customthe solvents were removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 1M HCl and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-57b8c2403f904751a4f2b17a1e240004
Source dataset
uspto-grants-2002_08
Patent number
US06436962B1

Reaction notes

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