反应详情

To 25 ml of fuming nitric acid was added 2.50 g of methyl 5-cyano-2-hydroxybenzoate. This solution quickly turned dark orange, and the reaction was complete after stirring for 1 h. The solution was slowly transferred to 100 ml of ice-cold water. To the resultant suspension was added 100 ml of ethyl acetate and the biphasic mixture was shaken and separated. The aqueous layer was extracted with ethyl acetate (2×60 ml), and the combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was taken up in ethyl acetate (100 ml) and filtered through a small plug of silica gel, eluting with more ethyl acetate (50 ml). The eluent was concentrated in vacuo to provide the title compound (2.71 g, 87%). Mass spectrum (ESI) 221.2 (M−1).

1. stirringthe biphasic mixture was shaken
2. customseparated
3. extractionThe aqueous layer was extracted with ethyl acetate (2×60 ml)
4. dry with materialthe combined organics were dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. filtrationfiltered through a small plug of silica gel
8. washeluting with more ethyl acetate (50 ml)
9. concentrationThe eluent was concentrated in vacuo