Water → 4-Cyanobenzoic acid

Participants

Reaction Conditions

Reaction Steps

Terephthalonitrile (12.8 g), sodium hydroxide (2.4 g), water (1.5 g), tert-butyl alcohol (300 ml) were mixed, and the resultant mixture stirred vigorously at 80° C. After the solvent was removed through distillation, sodium nitrite (16.6 g), acetic acid (250 ml), and acetic anhydride (25 ml) were added to the residue, and the resultant mixture was stirred vigorously at 5° C. Trifluoroacetic acid (27 g) was added dropwise to the mixture over three hours, and the mixture was further stirred vigorously for five hours. The solvent was removed through distillation under reduced pressure, and water (500 ml) was added to the residue. Sodium hydroxide was added to the solution under cooling with ice so as to adjust the pH to 8. After insoluble matter was removed through filtration, concentrated sulfuric acid was added to the filtrate under cooling with ice so as to adjust the pH to 4. Precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 10.6 g of p-cyanobenzoic acid (yield 72%). The obtained p-cyanobenzoic acid had a purity of 95%.

Provenance & Evidence