Ethanol → Diethyl 2,2'-(1,2-phenylene)diacetate

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Reaction Steps

1,2-phenylenediacetonitrile (1.0 g, 6.40 mmol) was dissolved in 5 ml ethyl alcohol and 2 ml concentrated sulfuric acid in a 25 ml round bottom flask. The mixture was stirred and heated to reflux for 6 hours. After neutralizing the reaction solution with ammonium hydroxide, the result solution was extracted with ethyl acetate (3×50 ml). The organic phase was combined and dried with Na2SO4. Concentration of the ethyl acetate afforded a yellow liquid. Running column with hexane: acetyl acetate=10:1, got yellow liquid 1.13 g (70.6%). 1H NMR (DMSO-d6): δ 1.24(t, 6H, CH3), δ 3.7 (s, 4H, CH2CO), δ 4.16(q, 4H, OCH2), δ 7.3 (d, 4H, Ar—H).

Provenance & Evidence