Реакция #1256723

Уравнение реакции

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

Растворители

water

toluene

Условия реакции

Обработка

1. 1
   Температураthe mixture is heated
2. 2
   Температураunder reflux for 3 h
3. 3
   ДругоеAfter hydrolysis
4. 4
   Фильтрацияthe deposited precipitate is filtered off with suction
5. 5
   Промывкаwashed with toluene
6. 6
   Другоеdried
7. 7
   workup.DISSOLUTIONThe product is dissolved in 200 ml of acetone
8. 8
   Температураthe mixture is heated
9. 9
   Температураunder reflux for 5 h
10. 10
    ДругоеThe majority of the solvent is removed under reduced pressure
11. 11
    ДругоеThe aqueous phase is separated off
12. 12
    Экстракцияextracted with MTB ether
13. 13
    ПромывкаThe combined organic phases are washed with water
14. 14
    Сушкаdried over sodium sulfate
15. 15
    ДругоеThe solvent is removed under reduced pressure
16. 16
    Другоеthe crude product is recrystallised from ethanol

Методика

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).

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