2-Hydroxy-5-norbornene-2-carboxylic acid → 2-Hydroxybicyclo(2.2.1)heptane-2-carboxylic acid

HRID 1440492Notes

Reaction equation

HRID 1440492 reaction equation
[OH:1][C:2]1([C:9]([OH:11])=[O:10])[CH2:7][CH:6]2[CH2:8][CH:3]1[CH:4]=[CH:5]2.[H][H]>C(OCC)(=O)C.[C].[Pd]>[OH:1][C:2]1([C:9]([OH:11])=[O:10])[CH2:7][CH:6]2[CH2:8][CH:3]1[CH2:4][CH2:5]2

Participants

5

Reactant 2

HCID 125275652-Hydroxy-5-norbornene-2-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 123869462-Hydroxybicyclo(2.2.1)heptane-2-carboxylic acidYield 143.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In 100 ml of ethyl acetate, 10.0 g of the 2-hydroxy-5-norbornene-2-carboxylic acid of Formula (4a) obtained in Step b. was dissolved. To the resulting solution, 0.5 g of 10% palladium carbon was further added as a catalyst for catalytic hydrogenation. This solution was stirred for 2 hours in an atmosphere of hydrogen gas to carry out catalytic hydrogenation. After the reaction was completed, the catalyst was separated by filtration and the ethyl acetate was evaporated from the filtrate under reduced pressure to obtain 14.5 g of crude 2-hydroxynorbornane-2-carboxylic acid of Formula (5a).

Workup

  1. dissolutionwas dissolved
  2. customthe catalyst was separated by filtration
  3. customthe ethyl acetate was evaporated from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-b971acdd3e324e608cdd99e89b8ac8d0
Source dataset
uspto-grants-1996_03
Patent number
US05498799

Reaction notes

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