Sodium bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate → bicyclo2.2.1heptane-2,3-dicarboxylic acid, disodium salt

HRID 2180211Notes

Reaction equation

HRID 2180211 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH:3]([C:8]([O-:10])=[O:9])[CH:2]2[C:11]([O-:13])=[O:12].[Na+:14].[Na+]>O.[Pd]>[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+:14].[Na+:14]

Participants

4

Reactant 1

HCID 21908873Sodium bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To a solution of disodium bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (10.0 g) in water (100 g) was added 0.5 g palladium on activated carbon (5 wt %). The mixture was transferred into a Parr reactor and was subjected to hydrogenation (50 psi, room temperature) for 8 hours. The activated carbon was filtered out, and the water was removed in vacuo at 75° C. The resulting product (m.p>300° C.) was dried and milled. NMR and IR analyses were consistent with that of the expected structure.

Workup

  1. filtrationThe activated carbon was filtered out
  2. customthe water was removed in vacuo at 75° C
  3. customThe resulting product (m.p>300° C.) was dried
  4. custommilled

Sources & evidence

ORD record
ord-53e875bbdfdd412d868616d3cfb3750a
Source dataset
uspto-grants-2005_05
Patent number
US06887963B2

Reaction notes

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