Reaktion #1753963

Reaktionsgleichung

sodium hydrogensulfite

(3-[1,3]dioxolan-2-ylphenyl)phenyl-methanol

18-crown-6

potassium permanganate

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title compound

(3-[1,3]Dioxolan-2-ylphenyl)phenylmethanone

Lösungsmittel

water

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcool to room temperature
2. 2
   ExtraktionBasify with a solution of 1N sodium hydroxide (about 60 ml) and extract with dichloromethane
3. 3
   Waschenwash sequentially with distilled water and brine
4. 4
   Trocknendry (Na2SO4)
5. 5
   Filtrationfilter
6. 6
   Einengenconcentrate
7. 7
   Sonstigeto give a residue
8. 8
   WaschenChromatograph the residue eluting with EtOAc

Vorschrift

Combine (3-[1,3]dioxolan-2-ylphenyl)phenyl-methanol (5.0 g, 18.5 mmol) and 18-crown-6 (160 mg, 0.6 mmol) in dichloromethane. Add potassium permanganate (8.8 g, 55.5 mmol). Heat to about 40° C. After 4 hours, cool to room temperature add water and sodium hydrogensulfite (6.0 g). Basify with a solution of 1N sodium hydroxide (about 60 ml) and extract with dichloromethane. Combine the organic layers and wash sequentially with distilled water and brine and then dry (Na2SO4), filter, and concentrate to give a residue. Chromatograph the residue eluting with EtOAc to give the title compound.

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