Sulfuric Acid → HCID 23149682, compound

HRID 2355172Notes

Reaction equation

HRID 2355172 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]2

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 110420624-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid

Product 1

HCID 23149682HCID 23149682, compoundYield 157.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. customThe mixture was bubbled with isobutene for 5 minutes
  2. temperaturewhile chilled in a salt/ice bath
  3. waitwas left for 4 days
  4. additionSubsequently, the reaction mixture was diluted with dichloromethane (5 mL)
  5. washwashed sequentially with a saturated aqueous solution of sodium bicarbonate and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-bacd54da40164b73979d456c19d1b7cc
Source dataset
uspto-grants-2010_07
Patent number
US07754757B2

Reaction notes

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