反应详情

温度

75 °C

2-methoxy-5-nitrophenol (50 g, 0.30 mol) was combined with 250 mL isopropyl alcohol. 1N sodium hydroxide solution, 310 mL (0.31 mol), was added to the mixture at such a rate that the temperature remained below 40° C. After the addition was completed, the mixture was stirred for at least 30 minutes. The reaction was then charged with 1-bromo-3-chloropropane (93.1 g, 0.59 mol) in a single portion. The mixture was heated to 75° C. and monitored periodically by high performance liquid chromatography (HPLC). After 8 hours, heating was discontinued and the reaction mixture was allowed to cool to ambient temperature overnight. The product gradually precipitated from the mixture as a light yellow/tan solid. Water, 200 mL, was added in a single portion and the resulting slurry was stirred for at least 30 minutes. The slurry was filtered and washed with water. The damp crude product was slurried in 650 mL methanol and heated to reflux until the solids had dissolved or mostly dissolved. The solution was allowed to cool gradually with stirring to ambient temperature over 3-5 hours or longer. The mixture was then cooled to 10-15° C. and held for at least 30 minutes. The solids were filtered and washed with cold methanol. The product was then dried in vacuo to give 60.3 g of 2-(3-chloropropoxy)-1-methoxy-4-nitrobenzene.

1. customremained below 40° C
2. additionAfter the addition
3. temperatureheating
4. temperatureto cool to ambient temperature overnight
5. customThe product gradually precipitated from the mixture as a light yellow/tan solid
6. additionWater, 200 mL, was added in a single portion
7. stirringthe resulting slurry was stirred for at least 30 minutes
8. filtrationThe slurry was filtered
9. washwashed with water
10. temperatureheated
11. temperatureto reflux until the solids
12. dissolutionhad dissolved
13. dissolutionmostly dissolved
14. temperatureto cool gradually
15. stirringwith stirring to ambient temperature over 3-5 hours or longer
16. temperatureThe mixture was then cooled to 10-15° C.
17. waitheld for at least 30 minutes
18. filtrationThe solids were filtered
19. washwashed with cold methanol
20. customThe product was then dried in vacuo