Reaktion #1232

Reaktionsgleichung

potassium iodide

sulfuric acid

sodium nitrite

3-methyl-4-aminobenzoic acid

sulfuric acid

→

3-methyl-4-iodobenzoic acid

Lösungsmittel

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThis solution was introduced dropwise via a dropping funnel
2. 2
   workup.STIRRINGThe mixture was stirred for eight hours
3. 3
   SonstigeThe solids obtained
4. 4
   Waschenwashed with water
5. 5
   Trocknenwith a sodium sulfite solution, dried over magnesium sulfate
6. 6
   Sonstigeevaporated
7. 7
   Sonstige24.4 g (70%) of 3-methyl-4-iodobenzoic acid of melting point 205°-210° C. were recovered

Vorschrift

20 g (0.132 mol) of 3-methyl-4-aminobenzoic acid and 175 ml of sulfuric acid (20%) were introduced into a three-necked flask. At -10° C., a solution of 11.9 g (0.172 mol) of sodium nitrite in 50 ml of water was added dropwise and the mixture was stirred for two hours. This solution was introduced dropwise via a dropping funnel cooled to -5° C. into a solution of 35 g (0.211 mol) of potassium iodide, 35.2 g (0.185 mol) of copper iodide and 175 ml of sulfuric acid (20%). The mixture was stirred for eight hours, and the reaction medium filtered. The solids obtained were dissolved in ethyl acetate, washed with water and then with a sodium sulfite solution, dried over magnesium sulfate and evaporated. 24.4 g (70%) of 3-methyl-4-iodobenzoic acid of melting point 205°-210° C. were recovered.

Quelle