Sodium Hydroxide → 2-Oxatricyclo[3.3.1.13,7]decane-1-carboxylic acid

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Reaction Steps

To a solution of 2-oxatricyclo[3.3.1.13,7]decane-1-carboxylic acid methyl ester (2.5 g, 12.6 mmol, prepared as described by Partch, R.; Brewster, W.; Stokes, B., Croatia Chemical Acta (1969), 58(4), 661-669) in 1:1 methanol/water (100 mL) was added 5 N aqueous NaOH (3.8 mL, 19 mmol). The mixture was stirred at room temperature for 3 hours and then extracted with methylene chloride to remove unreacted starting material. The aqueous layer was acidified (pH˜2) with 6 N aqueous HCl and then extracted with methylene chloride. The combined acidic extracts were dried (Na2SO4), filtered and concentrated to afford 1.92 g of the title compound. MS (ESI+) m/z 183 (M+H)+.

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