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

HRID 10483

Reaction equation

HRID 10483 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. Water is removed in vacuo at 75° C. The resulting product was dried and milled (m.p >300° C.).

Workup

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

Sources & evidence

ORD record
ord-2f21ab4ae6b24aae8d92c7c7db426ccc
Source dataset
uspto-grants-2006_08
Patent number
US07094820B2

Linked notes

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