反应详情

A mixture of 4-acetamidophenol (182.2 g, 1.2 moles), bromochloropropane (157.4 g, 1.0 mole), and potassium carbonate (145.0 g, 1.05 moles) was refluxed overnight in 700 ml of acetone. The acetone solution formed white crystals after being placed in a refrigerator overnight. The solution was filtered and the crystals washed with acetone. The filtrate was stripped to dryness, and the residue dissolved in chloroform and extracted with a 5% sodium hydroxide solution. Removal of the chloroform gave an oil. The white crystals obtained earlier were also dissolved in chloroform and extracted with a 5% sodium hydroxide solution. Removal of the chloroform gave a white solid. The white solid and oil were combined with acetone and placed in a refrigerator; white crystals were obtained. A 5-g sample of the white solid was recrystallized from acetone a second time to furnish 1.76 g (after drying in vacuo overnight at 80° C.) (23% yield) of white crystalline product, m.p. 125°-127° C.

1. customafter being placed in a refrigerator overnight
2. filtrationThe solution was filtered
3. washthe crystals washed with acetone
4. dissolutionthe residue dissolved in chloroform
5. extractionextracted with a 5% sodium hydroxide solution
6. customRemoval of the chloroform
7. customgave an oil
8. customThe white crystals obtained earlier
9. extractionextracted with a 5% sodium hydroxide solution
10. customRemoval of the chloroform
11. customgave a white solid
12. customwhite crystals were obtained
13. customA 5-g sample of the white solid was recrystallized from acetone a second time
14. customto furnish