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 (Richard, Partch; William, Brewster; Bruce, Stokes; Croatia Chemical Acta (1969), 58(4), 661-669) (2.5 g, 12.6 mmol) in methanol/water (1:1, 100 mL) was added aqueous 5N NaOH solution (3.8 mL, 19 mmol). The mixture was stirred at room temperature for three hours and then extracted with methylene chloride to remove unreacted starting material. The aqueous layer was acidified (pH˜2) with 6N HCl and then extracted with methylene chloride. The combined organic extracts were dried (Na2SO4), filtered, and concentrated to provide the title compound. MS (ESI+) m/z 183 (M+H)+ . . . .

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