Methanol → Bicyclo[2.2.1]hept-5-ene-2,2-dicarboxylic acid

HRID 67940Notes

Reaction equation

HRID 67940 reaction equation
CO.[OH-].[Na+].C([O:7][C:8]([C:10]1([C:17]([O:19]CC)=[O:18])[CH2:15][CH:14]2[CH2:16][CH:11]1[CH:12]=[CH:13]2)=[O:9])C>O1CCCC1>[C:17]([C:10]1([C:8]([OH:9])=[O:7])[CH2:15][CH:14]2[CH2:16][CH:11]1[CH:12]=[CH:13]2)([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 12548507Diethyl bicyclo[2.2.1]hept-5-ene-2,2-dicarboxylate

Product 1

HCID 12300923Bicyclo[2.2.1]hept-5-ene-2,2-dicarboxylic acidYield 89.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methanol (12 ml), 10% aqueous sodium hydroxide (12 ml), tetrahydrofuran (12 ml) and 2,2-bisethoxycarbonyl-5-norbornene (2.38 g) was stirred at room temperature for 24 hours and concentrated under reduced pressure. The residue was diluted with water, made acidic with 10% hydrochloric acid (HCl) solution and extracted with ether. The extract was washed with water and dried. Removal of the solvent gave as an oil 2,2-dicarboxy-5-norbornene (Compound No. 2-1) (1.63 g). IRνmaxfilm (cm-1): 2990, 1710, 1340.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with ether
  4. washThe extract was washed with water
  5. customdried
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-80c5da789ee64afab4af75dac655b382
Source dataset
uspto-grants-1982_08
Patent number
US04347254

Reaction notes

Loading…