Sodium Hydroxide → Spiro(2.5)octane-1-carboxylic Acid

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Reaction Steps

The product from Example 1A in 100 mL of water was treated with NaOH (11.4 g, 0.29 mol) and heated at reflux for 8 hours. The reaction mixture was allowed to cool to ambient temperature and extracted with diethyl ether (2×100 mL). The aqueous layer was acidified to pH 3 by careful addition of concentrated HCl and extracted with diethyl ether (3×100 mL). The ethereal extracts were combined and concentrated under reduced pressure to afford an oil that was distilled under vacuum (120° C., 60 torr) to provide the title compound as a clear oil. 1H NMR (CDCl3, 300 MHz) δ 11.95 (s, 1H), 1.30-1.60 (m, 11H), 1.13 (dd, 1H), 0.90 (dd, 1H); 13C NMR (CDCl3, 100 MHz) δ 179.6, 37.5, 32.1, 28.8, 26.0, 25.9, 25.6, 21.6; MS m/z 172 (M+NH4)+.

Provenance & Evidence