Ethanol → Diethyl 2-(4-methylphenoxy)-3-oxobutanedioate

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A sample of ethanol-free sodium ethoxide was prepared by dissolving sodium (3.0 g, 0.13 mole) in ethanol (50 ml) and then evaporating off the excess solvent. The last traces of ethanol were removed by the addition of dry toluene (50 ml), followed by evaporation to dryness. A stirred suspension of the white solid in dry ether (150 ml) under nitrogen, was treated dropwise with diethyl oxalate (17.6 ml, 0.13 mole) and the yellow solution allowed to stir for 21/2 hours at room temperature. A solution of the ethyl phenoxyacetate (0.13 mole, (D28)) in dry ether (50 ml) was added dropwise and the reaction mixture was left to stir overnight, before pouring into water (500 ml). The aqueous layer was separated, washed with ether (1×150 ml) and then acidified with dilute hydrochloric acid. The aqueous mixture was extracted with ether (3×150 ml) and the organic solution then washed with water (2×150 ml), dried (MgSO4) and evaporated to dryness to give the title compound as a yellow oil (28 g, 73%).

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