Diethyl Oxalate → HCID 87349868, compound

Participants

Reaction Steps

The method of Example II in U.S. Pat. No. 2,343,808 was used. Molten HMDA (27.1 grams) was poured into a solution of diethyl oxalate (136 grams) in ethanol (127 mL) and stirred for 18 hours. The solid was collected by filtration, dissolved in CH2Cl2 (150 mL) and purified by flash column chromatography (EtOAc as the eluent). The resulting solid was boiled in MTBE (150 mL), cooled to ambient temperature, and then collected by filtration to obtain 19.8 grams of hexamethylene-bis-oxamic acid ethyl ester as white needles having a melting point in the range of 91.6 to 92.5° C. 1H NMR (CDCl3, 300 MHz) δ 7.13 (brs, 2H), 4.34 (q, J=7.2 Hz, 4H), 3.33 (q, J=6.9 Hz, 4H), 1.59-1.52 (m, 4H), 1.37 (t, J=7.2 Hz, 6H), 1.39-1.34 (m, 4H).

Provenance & Evidence