Potassium Carbonate → 5-Methoxy-4,4-dimethyl-5-oxopentanoic acid

Participants

Reaction Steps

To a solution of dimethyl 2,2-dimethylpentanedioate from Step A (25.4 g, 135 mol) in MeOH (150 mL), THF (100 mL) and water (100 mL), was added potassium carbonate (36.2 g, 262 mmol). This biphasic solution was allowed to stir for 68 h, at ambient temperature, after which time the reaction was about 50% complete. Solvents were carefully removed in vacuo such that the starting materials did not vaporize. The aqueous layer was diluted with water (266 mL) and then extracted exhaustively with diethyl ether. The aqueous layer was made acidic by the addition of 6 M HCl (95 mL), saturated with NaCl, and extracted with diethyl ether (250 mL). This ethereal layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound. MS: m/z=175 (M+1).

Provenance & Evidence