Reaction #1483122

Reaction equation

potassium carbonate

9-(2-formylphenyl)phenanthrene

→

benzo[g]chrysene

Yield 44.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGStirring
2. 2
   workup.ADDITIONwas added
3. 3
   OtherAn aqueous phase was removed
4. 4
   Otheran organic phase which had been separated
5. 5
   Washwas washed with water and saturated brine
6. 6
   Dryingdried with magnesium sulfate
7. 7
   FiltrationAfter the magnesium sulfate was filtered out
8. 8
   Concentrationthe organic phase was concentrated
9. 9
   OtherThe resulting residue was purified by means of silica gel column chromatography

Procedure

24.0 g of the resulting 9-(2-formylphenyl)phenanthrene and 100 mL of dichloromethane were placed in a flask. During stirring at room temperature, 6 drops of methanesulfonic acid were added to the flask by means of a Pasteur pipette. Stirring was conducted at room temperature for further 8 hours. After the completion of the reaction, 100 mL of a 10% aqueous solution of potassium carbonate was added. An aqueous phase was removed and an organic phase which had been separated was washed with water and saturated brine, and then dried with magnesium sulfate. After the magnesium sulfate was filtered out, the organic phase was concentrated. The resulting residue was purified by means of silica gel column chromatography, whereby 5.21 g (yield: 25%) of benzo[g]chrysene was obtained.

Source