反应详情

温度

60 °C

To a solution of 2-hydroxy-3-nitrobenzoic acid (36.6 g) in N,N-dimethylformamide (500 mL) were added benzyl bromide (50.0 mL) and potassium carbonate (66.3 g), and the mixture was stirred overnight at 60° C. The reaction mixture was poured into water and the resulting mixture was extracted with a mixture of ethyl acetate and n-hexane (1:1). The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was dissolved in a mixture of tetrahydrofuran (100 mL) and methanol (200 mL), and the resulting mixture was stirred for 30 minutes at 50° C. The reaction mixture was concentrated and the residue was acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from isopropanol (50 mL)/n-hexane (200 mL) to give the title compound (31.99 g) having the following physical data.

1. extractionthe resulting mixture was extracted with a mixture of ethyl acetate and n-hexane (1:1)
2. washThe organic layer was washed with water and saturated brine
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated
5. dissolutionThe residue was dissolved in a mixture of tetrahydrofuran (100 mL) and methanol (200 mL)
6. stirringthe resulting mixture was stirred for 30 minutes at 50° C
7. concentrationThe reaction mixture was concentrated
8. extractionextracted with ethyl acetate
9. washThe organic layer was washed with water and saturated brine
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated
12. customThe residue was recrystallized from isopropanol (50 mL)/n-hexane (200 mL)