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

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Reaction Steps

To a solution of 2-oxa-tricyclo[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 5 N NaOH solution (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 (pH2) with 6 N HCl and then extracted with methylene chloride. This organic extract was dried (Na2SO4), filtered and concentrated to provide 1.92 g of the title compound as white crystalline solid. MS (ESI+) m/z 183 (M+H)+.

Provenance & Evidence