Reaction #1459020

Reaction equation

sodium hydrogensulfite

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

18-crown-6

potassium permanganate

→

title compound

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

Solvents

water

dichloromethane

Conditions

Workup

1. 1
   Temperaturecool to room temperature
2. 2
   ExtractionBasify with a solution of 1N sodium hydroxide (about 60 ml) and extract with dichloromethane
3. 3
   Washwash sequentially with distilled water and brine
4. 4
   Dryingdry (Na2SO4)
5. 5
   Filtrationfilter
6. 6
   Concentrationconcentrate
7. 7
   Otherto give a residue
8. 8
   WashChromatograph the residue eluting with EtOAc

Procedure

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.

Source