Sulfuric Acid → Bicyclo[2.2.1]heptane-2,3-dicarboxylic acid

HRID 1359187Notes

Reaction equation

HRID 1359187 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:8]([O-:10])=[O:9])[CH:2]2[C:11]([O-:13])=[O:12].[Na+].[Na+].S(=O)(=O)(O)O>O>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:8]([OH:10])=[O:9])[CH:2]2[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 21981355bicyclo2.2.1heptane-2,3-dicarboxylic acid, disodium salt

Product 1

HCID 99835Bicyclo[2.2.1]heptane-2,3-dicarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100.0 g (438.3 mmoles) of disodium bicyclo[2.2.1]heptane-2,3-dicarboxylate (228.15 g/mole) and 280 ml of water were charged into a 2L Erlenmeyer flask with stirring. To this solution was added fuming sulfuric acid until the pH of the resulting solution was ˜1. As the pH became acidic, a white flocculent precipitate formed. The solution was stirred and cooled to room temperature. The precipitate was removed by vacuum filtration and dried overnight in a vacuum oven at 110° C. The resulting product (melting point of 152.1-153.4° C.) was dried and milled. An IR analysis was consistent with that of the expected structure.

Workup

  1. additionTo this solution was added
  2. customa white flocculent precipitate formed
  3. stirringThe solution was stirred
  4. customThe precipitate was removed by vacuum filtration
  5. customdried overnight in a vacuum oven at 110° C
  6. dry with materialThe resulting product (melting point of 152.1-153.4° C.) was dried
  7. custommilled

Sources & evidence

ORD record
ord-a3d9a6992c184dfea2864462bfdcda9b
Source dataset
uspto-grants-2003_07
Patent number
US06599968B2

Reaction notes

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