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

HRID 1861894Notes

Reaction equation

HRID 1861894 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, from example 3) 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 was dried and milled (m.p >300 ° C. ). 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 was dried
  4. custommilled (m.p >300 ° C. )

Sources & evidence

ORD record
ord-e31a84dcbeed459d959145b1d14e6c96
Source dataset
uspto-grants-2003_03
Patent number
US06534574B1

Reaction notes

Loading…