Sodium Azide → p-Azidomethylphenylacetic acid

Participants

Reaction Steps

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).

Provenance & Evidence