反应详情

A slurry of NaH (16.0 g, 50% oily dispersion, 337 mM) in dimethylformamide (200 ml) was treated dropwise with a solution of 2-hydroxy-3-methoxy-6-nitrobenzaldehyde (49.0 g, 248 mM) in DMF (300 ml) at such a rate that the temperature did not exceed 35° C. The mixture is aged at room temperature for 1 hour and then a large excess of methyl iodide (100 ml) is added dropwise. A slight exothermic reaction occurs. The mixture is then stirred vigorously for 19 hours at room temperature. After the removal of excess methyl iodide, the reaction mixture is poured into ice-water (1 l). The crude product, a brown solid, is filtered, washed with cold water, and then recrystallized from isopropyl alcohol (700 ml) to afford the product as a tan solid; yield 27.9 g (53.3%); m.p. 106°-108° C.

1. customdid not exceed 35° C
2. customA slight exothermic reaction
3. customAfter the removal of excess methyl iodide
4. additionthe reaction mixture is poured into ice-water (1 l)
5. filtrationThe crude product, a brown solid, is filtered
6. washwashed with cold water
7. customrecrystallized from isopropyl alcohol (700 ml)