Reacción #319622

Ecuación de reacción

hydrochloric acid

aniline

sodium nitrite

tetronic acid

sodium acetate trihydrate

→

3-phenylazo-4-hydroxyfuran-2(5H)-one

Disolventes

—

ice water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroequipped with a 250-ml
2. 2
   workup.ADDITIONAfter this addition a yellow solid
3. 3
   Otroimmediately precipitated
4. 4
   workup.STIRRINGThe reaction mixture was stirred at 10° C. for 1.5 hours
5. 5
   Filtraciónfiltered off
6. 6
   Lavadoand the product was washed with 500 ml of cold methanol
7. 7
   OtroIt was dried at 35° C. in a vacuum

Procedimiento

300 ml of 6N hydrochloric acid solution was placed in a 1.5-liter flask equipped with a 250-ml dropping funnel, a mechanical stirrer and a thermometer. 57.6 g (0.61 mol) of distilled aniline was added with ice cooling. A solution of 43.92 g (0.64 mol) of sodium nitrite in 90 ml of ice water was added dropwise the resulting suspension and stirred for 40 min. The resultant diazonium salt solution was added dropwise to a solution of 60 g (0.6 mol) of tetronic acid and 120 g (0.88 mol) of sodium acetate trihydrate in 900 ml of water for 30 min. After this addition a yellow solid immediately precipitated. The reaction mixture was stirred at 10° C. for 1.5 hours, and filtered off; and the product was washed with 500 ml of cold methanol. It was dried at 35° C. in a vacuum. Concerning the product: Yield: 113.2 g = 92.4 percent. Melting point: 199°-200° C. (decomp.).

Fuente