Reaction #1178403

Reaction equation

1,3-Diphenylacetone

5-bromoacenaphthenequinone

KOH

→

3-Bromo-7,9-diphenyl-8H-Cyclopent[a]acenaphthylen-8-one

Solvents

methanol

Conditions

Workup

1. 1
   Otherprecipitated immediately
2. 2
   workup.STIRRINGThe mixture was then stirred at 65° C. for 1 hour
3. 3
   Temperaturecooled
4. 4
   Filtrationfiltered
5. 5
   WashThe black solid was washed well with methanol, ether
6. 6
   Otherdried

Procedure

1,3-Diphenylacetone (17.5 g, 83 mMole) was dissolved in methanol (240 mL) and heated to 65° C. To the solution was added 5-bromoacenaphthenequinone (2), (20 g, 75 mMole). The resulting well-stirred suspension was then treated with 1M-methanolic KOH (100 ML, 100 mMole) at a fast drip rate, whereupon the dark colored product precipitated immediately. The mixture was then stirred at 65° C. for 1 hour, cooled and filtered. The black solid was washed well with methanol, ether and dried. Yield of product (3), (31 g).

Source