Sodium Hydroxide → spiro[3.3]heptane-2,2-dicarboxylic acid

Participants

Reaction Conditions

Reaction Steps

A solution of diisopropyl spiro[3.3]heptane-2,2-dicarboxylate (2.85 g, 10.62 mmol) in MeOH (20 mL) was treated with 2N NaOH (31.9 mL, 63.7 mmol) and heated at 50° C. overnight. The organics were removed under reduced pressure, the aqueous residue acidified with 3M HCl, cooled to 5° C. and the solid collected via filtration. The filtrate was extracted with DCM (2×), then EtOAc (2×) and the combined organics were dried over Na2SO4, concentrated to dryness and combined with the first solid to afford spiro[3.3]heptane-2,2-dicarboxylic acid (1.737 g, 89%). 1H NMR (400 MHz, DMSO-d6): δ 12.58 (s, 2H), 2.39 (s, 4H), 1.91 (t, J=7.5 Hz, 4H), 1.71 (m, 2H).

Provenance & Evidence