反应详情

温度

100 °C

To a solution of 5-hydroxy-2-nitrobenzaldehyde (84.0 g) and ethyl 4-bromobutyrate (86 ml) in dry dimethylformamide (500 ml) blanketed under dry nitrogen was added potassium carbonate (76.0 g). The reaction mixture was heated to 100° C. for 1 hour. This mixture was cooled, and the solvent removed by evaporation to give a dark brown syrup. This residue was partitioned between ethyl acetate and saturated sodium carbonate (500 ml each). The organic layer was washed with additional saturated sodium carbonate (3×500 ml), and with brine (2×500 ml), dried, filtered and evaporated to give a dark brown syrup. Kugelrohr distillation (180° C., 0.2 mm) afforded ethyl 4-((3-formyl-4-nitrophenyl)oxy)butyrate (95 g) as a bright yellow syrup which slowly darkened upon standing.

1. temperatureThis mixture was cooled
2. customthe solvent removed by evaporation
3. customto give a dark brown syrup
4. customThis residue was partitioned between ethyl acetate and saturated sodium carbonate (500 ml each)
5. washThe organic layer was washed with additional saturated sodium carbonate (3×500 ml)
6. dry with materialwith brine (2×500 ml), dried
7. filtrationfiltered
8. customevaporated
9. customto give a dark brown syrup
10. distillationKugelrohr distillation (180° C., 0.2 mm)