Reaktion #595184

Reaktionsgleichung

2-bromo-1,3-dimethylbenzene

4-hydroxyindan-1-one

potassium carbonate

pyridine

→

title compound

Ausbeute 2.2%

4-(2,6-dimethylphenoxy)indan-1-one

Ausbeute 2.2%

Lösungsmittel

o-xylene

methanol

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling the reaction mixture
2. 2
   FiltrationThe insoluble material was filtered off
3. 3
   Einengenthe filtrate was concentrated
4. 4
   workup.ADDITIONWater was added to the residue
5. 5
   Extraktionthe mixture was extracted with ethyl acetate
6. 6
   WaschenThe organic layer was washed with 1 M hydrochloric acid, water and saturated brine
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   workup.ADDITIONChloroform was added to the residue
10. 10
    Filtrationthe insoluble material was filtered off
11. 11
    Sonstigethe filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=90/10-hexane/ethyl acetate=0/100)

Vorschrift

A mixture of 2-bromo-1,3-dimethylbenzene (15.0 g, 81.1 mmol), 4-hydroxyindan-1-one (10.0 g, 67.5 mmol), copper(II) oxide (9.13 g, 114 mmol), potassium carbonate (18.7 g, 135 mmol), pyridine (200 mL) and o-xylene (100 mL) was stirred under a nitrogen atmosphere at 130° C. for 18 hr. After cooling the reaction mixture, a mixed solvent of toluene and methanol was added. The insoluble material was filtered off, and the filtrate was concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1 M hydrochloric acid, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Chloroform was added to the residue, the insoluble material was filtered off and the filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=90/10-hexane/ethyl acetate=0/100) to give the title compound (0.373 g, yield 2%) as a yellow oil.

Quelle