反応 #1256723

反応方程式

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

溶媒

water

toluene

反応条件

後処理

1. 1
   温度the mixture is heated
2. 2
   温度under reflux for 3 h
3. 3
   その他After hydrolysis
4. 4
   ろ過the deposited precipitate is filtered off with suction
5. 5
   洗浄washed with toluene
6. 6
   その他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
    その他The majority of the solvent is removed under reduced pressure
11. 11
    その他The aqueous phase is separated off
12. 12
    抽出extracted with MTB ether
13. 13
    洗浄The combined organic phases are washed with water
14. 14
    乾燥dried over sodium sulfate
15. 15
    その他The solvent is removed under reduced pressure
16. 16
    その他the crude product is recrystallised from ethanol

実験手順

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).

出典