Sulfuric Acid → HCID 23149682, compound
Reaction equation
[C:1]12([C:12]([O:14][CH3:15])=[O:13])[CH2:8][CH2:7][C:4]([C:9]([OH:11])=[O:10])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.S(=O)(=O)(O)O>ClCCl>[C:4]12([C:9]([O:11][C:1]([CH3:8])([CH3:6])[CH3:2])=[O:10])[CH2:3][CH2:2][C:1]([C:12]([O:14][CH3:15])=[O:13])([CH2:6][CH2:5]1)[CH2:8][CH2:7]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl hydrogen bicyclo[2.2.2]octane-1,4-dicarboxylate (500 mg) was dissolved in dichloromethane (5 mL) and sulfuric acid (50 μL) was added to the solution. The mixture was bubbled with isobutene for 5 minutes while chilled in a salt/ice bath. The mixture was then stirred for 4 hours at room temperature and was left for 4 days. Subsequently, the reaction mixture was diluted with dichloromethane (5 mL), washed sequentially with a saturated aqueous solution of sodium bicarbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dried under reduced pressure to give 1,1-dimethylethyl methyl bicyclo[2.2.2]octane-1,4-dicarboxylate (497 mg).