Sodium Carbonate → 1,4,4a,5,6,7,8,8a-Octahydro-5-methyl-1,4-methanonaphthalen-5-yl formate
Reaction equation
[CH3:1][C:2]1([OH:13])[CH2:11][CH2:10][CH2:9][CH:8]2[CH:3]1[CH:4]1[CH2:12][CH:7]2[CH:6]=[CH:5]1.[C:14]([O-])([O-])=[O:15].[Na+].[Na+]>>[CH:14]([O:13][C:2]1([CH3:1])[CH2:11][CH2:10][CH2:9][CH:8]2[CH:3]1[CH:4]1[CH2:12][CH:7]2[CH:6]=[CH:5]1)=[O:15]Participants
3
Procedure
7.4 g (0.042 mole) of 3-methyl-tricyclo[6.2.1.02,7 ]undec-9-en-3-ol--see Example 1--were then added to the above mixture, and the whole mixture was stirred for 3 days at room temperature. The obtained mixture was then decomposed by the addition of 100 ml of a saturated aqueous solution of Na2CO3, extracted with ether (3×50 ml), washed with water (3×50 ml) and dried over Na2SO4. After evaporation 8 g of crude material were obtained which, by distillation at 0.02 Torr, provided the desired compound in a 58% yield.
Workup
- additionwere then added to the above mixture