Tetrahydrofuran → 5-Norbornene-2-carboxylic acid

19.0 g (58.5 mmol) of the Diels-Alder adduct was dissolved in 115 ml of tetrahydrofuran, 12.9 g (300 mmol) of sodium hydroxide in 140 ml of water was added on ice cooling, the mixture was stirred at room temperature for 24 hours. After distilling off tetrahydrofuran, the product was neutralized with 27 ml of concentrated hydrochloric acid and extracted with a mixture solvent of hexane-methylene chloride (98:2) (100 ml×4). The extract was dried over anhydrous magnesium sulfate, the solution was filtered, and the solvent was distilled off to obtain 8.3 g of crude 5-norbornene-2-carboxylic acid.

1. distillationAfter distilling off tetrahydrofuran
2. extractionextracted with a mixture solvent of hexane-methylene chloride (98:2) (100 ml×4)
3. dry with materialThe extract was dried over anhydrous magnesium sulfate
4. filtrationthe solution was filtered
5. distillationthe solvent was distilled off

ORD record

ord-69f6f5f24bf249ce927f595f9ffd26a4

Source dataset

uspto-grants-1993_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05266728