Sodium Hydroxide → Bicyclo[2.2.2]octane-2-carboxylic acid

Sodium hydroxide (2.5N, 22.4 mL, 56 mmol) was added to a methanolic solution of methyl bicyclo[2.2.2]octane-2-carboxylate (4.7 g, 28 mmol in 50 mL) at ambient temperature and the mixture was stirred for 16 hours. The solvent was concentrated in vacuo, water added (20 mL) and the solution made acidic with IN aqueous HCl. The product was extracted into dichloromethane (3×50 mL), the combined organic layers washed with water (25 mL), dried over anhydrous magnesium sulfate, filtered and concentrated on a rotary evaporator to afford the titled compound of formula (III) as a white solid (4.3 g, 100% yield).

1. concentrationThe solvent was concentrated in vacuo, water
2. additionadded (20 mL)
3. extractionThe product was extracted into dichloromethane (3×50 mL)
4. washthe combined organic layers washed with water (25 mL)
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated on a rotary evaporator

ORD record

ord-042ce404b760499cb2ff7dbcdc96da72

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07179813B2