Reaction #499061

Reaction equation

12-methoxycarbonylhexacyclo-[6.6.1.13,6.110,13.02,7.09,14]heptadecene

potassium hydroxide

→

12-carboxyhexacyclo[6.6.1.13,6.110,13.02,7.09,14]heptadecene

Yield 64.3%

Solvents

ethanol

Conditions

Workup

1. 1
   workup.ADDITIONwere added
2. 2
   Temperatureunder reflux
3. 3
   OtherTwo hours
4. 4
   Temperatureto cool down
5. 5
   Concentrationwas then concentrated
6. 6
   Otherin an evaporator
7. 7
   workup.ADDITIONWater (50 ml) and ether (50 ml) were added
8. 8
   Otherthe resultant water layer was separated
9. 9
   Othera white precipitate was formed
10. 10
    FiltrationThe precipitate was collected by filtration
11. 11
    Washwas then washed with water until the washing

Procedure

Next, 3.6 g of the 12-methoxycarbonylhexacyclo-[6.6.1.13,6.110,13.02,7.09,14]heptadecene were dissolved in 30 ml of 95% ethanol, into which 1.25 g of potassium hydroxide were added. The resultant mixture was then heated under reflux. Two hours later, the reaction mixture was allowed to cool down and was then concentrated to ⅓ volume in an evaporator. Water (50 ml) and ether (50 ml) were added, and the resultant water layer was separated. When the water layer was acidified with 3% HCl, a white precipitate was formed. The precipitate was collected by filtration and was then washed with water until the washing became neutral, whereby 2.2 g of 12-carboxyhexacyclo[6.6.1.13,6.110,13.02,7.09,14]heptadecene were obtained.

Source