Ethanol → 2-(2-Phenylethyl)malonic acid

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Reaction Steps

The diethyl benzylmethylmalonate (75 g) was combined with 300 ml of ethanol and a solution of 100 g of potassium hydroxide in 300 ml of water and heated at gentle reflux for 5 hours. After cooling, the mixture was extracted with diethyl ether (2×300 ml). The aqueous layer was then acidified with 120 ml of concentrated hydrochloric acid and extracted with diethyl ether (3×300 ml). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated to yield 49.2 g of benzylmethylmalonic acid as a yellow solid (83% yield).

Provenance & Evidence