Sulfuric Acid → HCID 23149682, compound

HRID 555676Notes

Reaction equation

HRID 555676 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-8b5f4acfc1e84fd582f0b6042e60787a
Source dataset
uspto-grants-2011_11
Patent number
US08053465B2

Reaction notes

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