Sodium Hydroxide → 2-Oxatricyclo[3.3.1.1,3,7]decane-1-carboxylic acid
Reaction equation
C[O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[O:6]1)[CH2:12]2)=[O:4].[OH-].[Na+]>CO.O>[C:5]12([C:3]([OH:4])=[O:2])[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[O:6]1)[CH2:12]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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)+.