Water → 5-Methoxy-4,4-dimethyl-5-oxopentanoic acid

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Reaction Steps

Dimethyl-2,2-dimethylglutarate (18.26 g, 97.0 mmol) and potassium carbonate (27.14 g, 196.4 mmol) were dissolved in 280 mL of 3:2:2 methanol:tetrahydrofuran:water. The reaction mixture was stirred at ambient temperature for 73 hours, and then concentrated in vacuo. The resulting residue was taken up in water. The aqueous phase was extracted twice with ethyl acetate, and the organic phase was discarded. The aqueous phase was then acidified with a 1.0M aqueous solution of hydrochloric acid, and extracted three times with ethyl acetate. The ethyl acetate layer was washed once with brine, dried over sodium sulfate, filtered, and the filtrate was evaporated to dryness to give the title compound as an oil.

Provenance & Evidence