Dimethyl oxalate → HCID 178501818, compound

Participants

Reaction Steps

To a well stirred suspension of freshly prepared sodium ethylate (820 mg, 12 mmol) in dry benzene (10 mL), 3,4-dichloroacetophenone (1.89 g, 10 mmol) and dimethyloxalate (1.18 g, 10 mmol) dissolved in dry benzene (20 mL), were added dropwise on cooling at +5° C., and under dry nitrogen atmosphere. The resulting dark red suspension was stirred at room temperature over 4 hours. The reaction mixture was then poured into ice/2N HCl (1:1 w/w), stirred for 5 minutes and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and concentrated in vacuo to afford a pale yellow solid, which was recrystallized from acetonitrile to yield the pure ester (2.4 g, 86%),colorless needles, mp. 122-123° C.

Provenance & Evidence