Sulfuric Acid → 4-Iodo-3-methylbenzoic acid

Participants

Reaction Steps

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. A solution of 11.9 g (0.172 mmol) of sodium nitrite in 50 ml of water was added dropwise at -10° C. and the mixture was stirred for 2 hours. This solution was introduced dropwise, via a funnel cooled at -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 8 hours, the reaction medium filtered, the solid obtained dissolved in ethyl acetate, washed with water and then with a solution of sodium sulfite, dried over magnesium sulfate and evaporated. 24.4 g (70%) of 3-methyl-4-iodobenzoic acid of melting point 205-10° C. were recovered.

Provenance & Evidence