Sodium Azide → p-Azidomethylphenylacetic acid

HRID 355251Notes

Reaction equation

HRID 355251 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[N-:13]=[N+:14]=[N-:15].[Na+]>CC(C)=O.O>[N:13]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)=[N+:14]=[N-:15]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 45190564-(Bromomethyl)phenylacetic acid

Product 1

HCID 14197001p-Azidomethylphenylacetic acidYield 71.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of p-bromomethylphenylacetic acid (3.64 g, 15.9 mmol) in acetone (100 ml) was treated with a solution of sodium azide (1.04 g, 16.0 mmol) in H2O (15 ml). The mixture was stirred at room temperature overnight (ca. 20 h). After evaporation of the acetone, the residual solution was cooled in an ice-bath. The white gelatinous precipitate that formed was collected, washed with cold water and dried yielding 2.175 g (11.4 mmol, 71.5%) of p-azidomethylphenylacetic acid as a white solid: 1Hmr (DMSO-d6) δ: 3.59 (2H, s, --CH2CO2), 4.42 (2H, s, --CH2N3) and 7.32 ppm (4H, s, aromatic Hs); ir (nujol) νmax : 2500-3400 (b, --CO2H), 2070 (s, --N3) and 1690 cm-1 (s, C=O).

Workup

  1. customAfter evaporation of the acetone
  2. temperaturethe residual solution was cooled in an ice-bath
  3. customThe white gelatinous precipitate that formed
  4. customwas collected
  5. washwashed with cold water
  6. customdried

Sources & evidence

ORD record
ord-7e699bfd262449dd8c378c1d86a45103
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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