Reaktion #571423

Reaktionsgleichung

aluminum bromide

acetate

HCl

benzene

benzene

methoxy indanone

→

title compound

6-Hydroxy-2-methyl-1-indanone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled in an ice bath
2. 2
   ExtraktionThe aqueous phase is extracted with ether (3 times)
3. 3
   Einengenthe extracts are concentrated at reduced pressure
4. 4
   Extraktionextracted with 2.5N-NaOH (2×75 mL and 1×50 mL)
5. 5
   Extraktionthe oil that separates is extracted with ether (3 times)
6. 6
   WaschenThe combined extracts are washed with brine
7. 7
   Trocknendried (MgSO4)
8. 8
   Sonstigeevaporated
9. 9
   Sonstigeto yield an oil that
10. 10
    Sonstigechromatographed (on silica Merck-60, gradient CH2Cl2, CH2Cl2 -ethyl acetate 85:15 )

Vorschrift

To a stirred solution of anhydrous aluminum bromide (69.82 g, 0.261 mole) in anhydrous benzene (250 mL) kept under nitrogen is added dropwise over 30 minutes a solution of the methoxy indanone (18 g, 0.102 mole) of Step C, in benzene (60 mL). The mixture is gently refluxed for 3 hours (TLC, dichloromethaneethyl acetate 8:2, UV), cooled in an ice bath and treated dropwise with 6N-HCl (ca. 200 mL) to decompose the aluminum complex. The aqueous phase is extracted with ether (3 times), the extracts are concentrated at reduced pressure and extracted with 2.5N-NaOH (2×75 mL and 1×50 mL). The basic extracts are neutralized (ice bath) with concentrated HCl and the oil that separates is extracted with ether (3 times). The combined extracts are washed with brine, dried (MgSO4) and evaporated to yield an oil that readily solidifies. The crude material is flash chromatographed (on silica Merck-60, gradient CH2Cl2, CH2Cl2 -ethyl acetate 85:15 ) to provide the pure title compound (13.60 g, nearly colorless solid, 82%).

Quelle