反应详情

温度

0 °C

2,4,6-Trimethylbenzoic acid (mesitoic acid) (10 g, 61 mmol) was suspended in 150 mL of water, and the mixture cooled to 0° C. Sodium hydroxide pellets (7.31 g, 0.18 mol) were gradually added, followed by addition of potassium permanganate (4×7.2 g, 0.18 mol) at four intervals of 30 minutes. The mixture was stirred at room temperature for 2 hours, then heated on a steam bath for 15-30 minutes. Sulfuric acid (200 mL, 9 mol) was added, then sodium bisulfite was carefully and gradually added at 0° C. The precipitated white solid was filtered and then dissolved in 5 N ammonium hydroxide. The solution was washed with diethyl ether, then gradually treated dropwise with concentrated sulfuric acid to precipitate the product. Filtration, followed by washing with hot water (4×) and petroleum ether (3×), recrystallization (methanol-water), and drying at high vacuum gave 10.5 g (89%) of the product as a white solid, m.p. >300° C. (ref. W. A. Noyes, Amer. Chem. J., 20, 789 (1898)).

1. additionwere gradually added
2. temperatureheated on a steam bath for 15-30 minutes
3. additiongradually added at 0° C
4. filtrationThe precipitated white solid was filtered
5. dissolutiondissolved in 5 N ammonium hydroxide
6. washThe solution was washed with diethyl ether
7. additiongradually treated dropwise with concentrated sulfuric acid
8. customto precipitate the product
9. filtrationFiltration
10. washby washing with hot water (4×) and petroleum ether (3×), recrystallization (methanol-water)
11. customdrying at high vacuum