Réaction #1256723

Équation de réaction

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

Solvants

water

toluene

Conditions de réaction

Traitement

1. 1
   Températurethe mixture is heated
2. 2
   Températureunder reflux for 3 h
3. 3
   AutreAfter hydrolysis
4. 4
   Filtrationthe deposited precipitate is filtered off with suction
5. 5
   Lavagewashed with toluene
6. 6
   Autredried
7. 7
   workup.DISSOLUTIONThe product is dissolved in 200 ml of acetone
8. 8
   Températurethe mixture is heated
9. 9
   Températureunder reflux for 5 h
10. 10
    AutreThe majority of the solvent is removed under reduced pressure
11. 11
    AutreThe aqueous phase is separated off
12. 12
    Extractionextracted with MTB ether
13. 13
    LavageThe combined organic phases are washed with water
14. 14
    Séchagedried over sodium sulfate
15. 15
    AutreThe solvent is removed under reduced pressure
16. 16
    Autrethe crude product is recrystallised from ethanol

Mode opératoire

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).

Source