Diethyl Oxalate → HCID 117727660, compound

Participants

Reaction Steps

To a suspension of 1-fluoro-5-methyl-2,4-dinitro-benzene (about 100.0 g, 0.5 mol) in methanol (about 1.5 L), sodium methoxide (about 108 g, 1.9 mol) and diethyl oxalate (about 136 mL, 1.0 mol) are added at a temperature of about −10° C. The resulting orange color suspension is slowly allowed to reach a temperature of about 15-20° C. in about 2 hours and continuous stirring is carried out at a temperature of about 15-20° C. over a period of about 32 hours. The reaction mixture is quenched with 1.5 N HCl (about 200 mL), the precipitated solid obtained is filtered and dried under vacuum to obtain the product [3-(5-methoxy-2,4-dinitro-phenyl)-2-oxo-propionic acid methyl ester] as pale yellow solid (about 125 g, 85%). 1H NMR (DMSO-d6, 300 MHz): 3.84 & 3.87 (2s, 3H), 4.02 & 4.04 (2s, 3H), 8.63 & 10.93 (s & bs, 2H), 7.56 & 8.07 (2s, 1H), 8.63 & 8.75 (2s, 1H); LC-MS (ESI): 297.0 (M-H).

Provenance & Evidence