反应详情

A mixture of diphenyliodonium-2-carboxylate monohydrate (11.4 g, 33.3 mmol), 3-amino-2-chloro-α-methylbenzenemethanol (5.2 g, 30.3 mmol), and cupric acetate (0.5 g) in isopropanol (100 mL) is heated at reflux for 12 hours under an argon atmosphere. The solvent is evaporated under vacuum and the remaining dark oil is taken up in 10% aqueous KOH. The insoluble material is removed by filtration through Celite-545, and the filtrate is extracted with ether to remove nonacidic impurities. The aqueous solution is acidified to pH=3 with concentrated HCl. The resulting precipitate is collected by filtration and purified by column chromatography (silica, ethyl acetate) to give pure 2-[[2-chloro-3-(1-hydroxyethyl)phenylamino]benzoic acid (5.8 g, 60%), mp=169-171° C.

1. temperatureis heated
2. temperatureat reflux for 12 hours under an argon atmosphere
3. customThe solvent is evaporated under vacuum
4. customThe insoluble material is removed by filtration through Celite-545
5. extractionthe filtrate is extracted with ether
6. customto remove nonacidic impurities
7. filtrationThe resulting precipitate is collected by filtration
8. custompurified by column chromatography (silica, ethyl acetate)