Hydrochloric Acid → Diethyl 2-acetyl-2-phenylmalonate

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Reaction Steps

To a solution of diethyl 2-phenylmalonate (100 mmol) in anhydrous tetrahydrofuran (300 mL) is added sodium ethoxide (110 mmol). The mixture is stirred at room temperature for 30 minutes, followed by the addition of a solution of acetyl chloride (110 mmol) in tetrahydrofuran (50 mL). After the addition is complete, the mixture is heated to reflux for 3 hours, cooled to room temperature, neutralized with 2 N HCl, then concentrated in vacuo. The residue is partitioned between H2O and CHCl3, the organic extracts washed with sodium bicarbonate, water, and brine, dried (MgSO4), filtered and concentrated.

Provenance & Evidence