Sodium Hydroxide → Bicyclo[2.2.1]heptane-2-carboxylic acid

5.00 g (20.0 mmol) of the Diels-Alder adduct obtained by the step 2 of Example 1 was dissolved in 45 ml of a mixture solvent of tetrahydrofuran-water (5:4), 1.85 g (43.0 mmol) of sodium hydroxide (93%) was added on ice cooling, and the mixture was stirred at room temperature for 24 hours. After tetrahydrofuran was distilled off, the reaction mixture was neutralized with concentrated hydrochloric acid. Then, 280 mg of 5% palladium-carbon powder was added and the mixture was stirred for 30 hours under an atmosphere of hydrogen. The catalyst was filtered off, the filtrate was acidified with concentrated hydrochloric acid and extracted with a mixture solvent of hexane-methylene chloride (98:2) (50 ml×4). The extract was dried over anhydrous magnesium sulfate and filtered, the solvent was distilled off, and 2.66 g of crude 2-norbornanecarboxylic acid was obtained. Crude yield: 95%.

1. custom5.00 g (20.0 mmol) of the Diels-Alder adduct obtained by the step 2 of Example 1
2. additionwas added on ice cooling
3. distillationAfter tetrahydrofuran was distilled off
4. additionThen, 280 mg of 5% palladium-carbon powder was added
5. stirringthe mixture was stirred for 30 hours under an atmosphere of hydrogen
6. filtrationThe catalyst was filtered off
7. extractionextracted with a mixture solvent of hexane-methylene chloride (98:2) (50 ml×4)
8. dry with materialThe extract was dried over anhydrous magnesium sulfate
9. filtrationfiltered
10. distillationthe solvent was distilled off

ORD-Eintrag

ord-b1d0595005bd447aa561e99cc3042a55

Quelldatensatz

uspto-grants-1993_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05266728