Benzyl Chloride → Diethyl dibenzylpropanedioate

Participants

Reaction Steps

Diethyl malonate (4.53 mL, 30.0 mmol) was added gradually at 0° C. to a mixed liquid containing sodium hydride (55 wt % in oil, 2.95 g, 67.5 mmol) and anhydrous N,N-dimethylformamide (60 mL). Following stirring of the resulting mixed liquid at this temperature for 30 minutes, benzyl chloride (7.25 mL, 63.0 mmol) was added. The resulting mixed liquid was stirred at room temperature for one hour, and a saturated aqueous solution of ammonium chloride was then added to halt the reaction. The organic layer was separated from the mixed liquid, and the water layer was extracted with ethyl acetate. The thus obtained organic layer was washed with a saturated saline solution and then dried using anhydrous magnesium sulfate, yielding the title compound (1a-1) in a yield of 95%.

Provenance & Evidence