反应详情

A mixture of 2-nitro-5-phenoxytoluene (57.3 g, 0.25 mol) prepared in Step A above and dimethylformamide dimethyl acetal (43.1 mL, 0.324 mol) in DMF (259 mL) was heated overnight at 140° C. The mixture was cooled to room temperature, and the solvent was evaporated in vacuo. The residue was dissolved in THF (500 mL) and transferred to a 3 L 3-neck flask equipped with an overhead stirrer. The mixture was diluted with 500 mL of water, and NalO4 (160 g, 0.75 mol) was added in portions (slight exotherm). The mixture was stirred overnight at room temperature. The solids were filtered and washed well with EtOAc. The filtrate was washed 3× with saturated aqueous NaHCO3 solution, and then dried (MgSO4). The solution was filtered and the solvent was evaporated in vacuo. The crude product was chromatographed (10-40% CH2Cl2:hexane) to yield 2-nitro-5-phenoxy-benzaldehyde as a yellow crystalline solid.

1. customthe solvent was evaporated in vacuo
2. dissolutionThe residue was dissolved in THF (500 mL)
3. customequipped with an overhead stirrer
4. additionThe mixture was diluted with 500 mL of water, and NalO4 (160 g, 0.75 mol)
5. additionwas added in portions (slight exotherm)
6. filtrationThe solids were filtered
7. washwashed well with EtOAc
8. washThe filtrate was washed 3× with saturated aqueous NaHCO3 solution
9. dry with materialdried (MgSO4)
10. filtrationThe solution was filtered
11. customthe solvent was evaporated in vacuo
12. customThe crude product was chromatographed (10-40% CH2Cl2:hexane)