Hydrochloric Acid → 1,3-Diethyl 2-[(2-iodophenyl)methyl]propanedioate

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Reaction Steps

Sodium (0.19 g, 8.2 mmol) was dissolved in absolute ethanol (12 mL). The solution was cooled on an ice bath. Malonic acid diethyl ester (1.3 g, 8.1 mmol) was added. A solution of 1-chloromethyl-2-iodo-benzene (2.0 g, 7.9 mmol) in absolute ethanol (6 mL) cooled on an ice bath was added to the malonic acid diethyl ester solution. The solution, which deposited sodium chloride, was let stand at 0° C. for 4 h and at room temperature overnight. The solution was neutralised with HCl (4N). The solvent was removed in vacuo and the residue was dissolved in dichloromethane (25 mL). Water (15 mL) was added and the phases were separated. The aqueous phase was reextracted with dichloromethane (10 mL). The combined organic fractions were dried (Na2SO4), filtered and evaporated. Yield: 2.86 g, 92%.

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