反应 #1256723

反应方程式

methyl 2-oxo-5-propylcyclohexanecarboxylate

resorcinol

phosphoryl chloride

potassium carbonate

ethyl iodide

→

3-ethoxy-8-propyl-7,8,9,10-tetrahydrobenzo[c]chromen-6-one

溶剂

water

toluene

反应条件

后处理

1. 1
   温度the mixture is heated
2. 2
   温度under reflux for 3 h
3. 3
   其他After hydrolysis
4. 4
   过滤the deposited precipitate is filtered off with suction
5. 5
   洗涤washed with toluene
6. 6
   其他dried
7. 7
   workup.DISSOLUTIONThe product is dissolved in 200 ml of acetone
8. 8
   温度the mixture is heated
9. 9
   温度under reflux for 5 h
10. 10
    其他The majority of the solvent is removed under reduced pressure
11. 11
    其他The aqueous phase is separated off
12. 12
    萃取extracted with MTB ether
13. 13
    洗涤The combined organic phases are washed with water
14. 14
    干燥dried over sodium sulfate
15. 15
    其他The solvent is removed under reduced pressure
16. 16
    其他the crude product is recrystallised from ethanol

实验过程

16.6 g (78.5 mmol) of methyl 2-oxo-5-propylcyclohexanecarboxylate, 7.65 g (69.5 mmol) of resorcinol and 5.6 ml (6.1 mmol) of phosphoryl chloride are dissolved in 55 ml of toluene, and the mixture is heated under reflux for 3 h. After hydrolysis using water, the deposited precipitate is filtered off with suction, washed with toluene and dried. The product is dissolved in 200 ml of acetone, 20 g (145 mmol) of potassium carbonate and 9.00 g (57.7 mmol) of ethyl iodide are added, and the mixture is heated under reflux for 5 h. The majority of the solvent is removed under reduced pressure, and the residue is taken up in MTB ether/water. The aqueous phase is separated off and extracted with MTB ether. The combined organic phases are washed with water and dried over sodium sulfate. The solvent is removed under reduced pressure, and the crude product is recrystallised from ethanol, giving 3-ethoxy-8-propyl-7,8,9,10-tetrahydrobenzo[c]chromen-6-one as colourless crystals. The melting point is 108° C. The other physical properties are: Δ∈=−7.5 (extrapolated from 5% solution in ZLI-2857), Δn=0.1302 (5% in ZLI-4792).

来源