Hydrochloric Acid → 1,4-Dioxaspiro[4.5]decane-8-carboxylic acid

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Reaction Steps

Ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate (79.58 mmol, 17.05 g) is taken up in 300 mL 2:1 THF:H2O in 500 mL roundbottom flask. Lithium hydroxide monohydrate (120 mmol, 5.01 g) and 100 mL MeOH were added to this solution. The reaction mixture was allowed to stir overnight at room temperature. The reaction mixture was acidified to pH 3 with 1N HCl(aq) and extracted with 100 mL DCM (×5). The combined organics were combined and then dried over Na2SO4, and the solvent was removed in vacuo to yield 1,4-dioxaspiro[4.5]decane-8-carboxylic acid (14.96 g, 100% yield) as white solid.

Provenance & Evidence