反应详情

Combine 2,6-dichloro-4-hydroxy-benzaldehyde (120 g, 628.24 mmol) and potassium carbonate (173.65 g, 1256.5 mmol) in 900 mL dimethylformamide and treat with iodomethane (107 g, 753.9 mmol). Stir the reaction at room temperature for 3 hours. Filter off solids and pour into 6 L of water. Filter solids, wash several times with water, air dry and dissolve in ethyl acetate. Wash with water, followed by brine and then dry over sodium sulfate. Filter and concentrate under vacuum to ˜100 mL volume, at which point, solids start to crash out. Filter then concentrate down the filtrate to yield a second crop. Wash with hexane, combine all solids and vacuum dry to yield 112.3 g of off-white, solid: 1H NMR (400 MHz, CDCl3) δ 10.41 (s, 1H), 6.90 (s, 2H), 3.87 (s, 3H).

1. customthe reaction at room temperature for 3 hours
2. filtrationFilter off solids
3. additionpour into 6 L of water
4. filtrationFilter solids
5. washwash several times with water, air
6. customdry
7. dissolutiondissolve in ethyl acetate
8. washWash with water
9. dry with materialdry over sodium sulfate
10. filtrationFilter
11. concentrationconcentrate under vacuum to ˜100 mL volume, at which point, solids
12. filtrationFilter
13. concentrationthen concentrate down the filtrate
14. customto yield a second crop
15. washWash with hexane
16. customdry
17. customto yield 112.3 g of off-white, solid