Reaction #96218

Reaction equation

methanol

sodium hydroxide

2,2-bisethoxycarbonyl-5-norbornene

→

2,2-dicarboxy-5-norbornene

Yield 89.6%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Concentrationconcentrated under reduced pressure
2. 2
   workup.ADDITIONThe residue was diluted with water
3. 3
   Extractionextracted with ether
4. 4
   WashThe extract was washed with water
5. 5
   Otherdried
6. 6
   OtherRemoval of the solvent

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.

Source