反应 #2069923

反应方程式

4-Isopropylaniline

potassium iodide

sodium nitrite

sulphuric acid

→

4-Isopropyliodobenzene

溶剂

water

water

water

反应条件

后处理

1. 1
   其他does not rise above 20° C
2. 2
   workup.ADDITIONOn completion of the dropwise addition
3. 3
   workup.STIRRINGThe reaction mixture is stirred at 80° C. for 1 h
4. 4
   温度After cooling
5. 5
   其他the organic phase is removed
6. 6
   萃取the aqueous phase is extracted four times more with 100 ml of ether
7. 7
   洗涤The combined organic phases are washed with dilute sodium hydroxide solution and dist
8. 8
   干燥water, and dried over sodium sulphate
9. 9
   其他After the solvent has been removed
10. 10
    workup.DISTILLATIONthe crude product is distilled in a membrane-pump vacuum
11. 11
    其他The slightly reddish target product distils over at a temperature of 100-105° C. (15 mbar)

实验过程

4-Isopropylaniline (49.5 g, 366 mmol) is suspended in 200 ml of dist. water and admixed gradually under ice cooling with 200 ml of semiconcentrated sulphuric acid. Subsequently, a solution of sodium nitrite (25.5 g, 370 mmol) in 200 ml dist. water is added dropwise at such a rate that the temperature does not rise above 20° C. On completion of the dropwise addition, the mixture is stirred at 2° C. for another 20 min. The resulting clear reddish diazonium salt solution is now added through a filter to a solution of potassium iodide (135.0 g, 813 mmol) in 200 ml of dist. water. The reaction mixture is stirred at 80° C. for 1 h. In the course of this, the solution becomes black with vigorous gas evolution and an oily organic phase separates out. After cooling, the organic phase is removed and the aqueous phase is extracted four times more with 100 ml of ether. The combined organic phases are washed with dilute sodium hydroxide solution and dist. water, and dried over sodium sulphate. After the solvent has been removed, the crude product is distilled in a membrane-pump vacuum. The slightly reddish target product distils over at a temperature of 100-105° C. (15 mbar).

来源