Diethyl Oxalate → Diethyl 2-oxo-3-phenylsuccinate

Participants

Reaction Steps

Ethyl atropate with a methyl atropate content not exceeding 0.05% can be obtained in a relatively complicated, two-stage process (Helv. Chim. Acta 30, 1349 (1947)) as long as the starting materials do not contain more than 0.05% of methyl compounds. This process involves ethyl phenylacetate being condensed with diethyl oxalate in the presence of sodium ethanolate to give diethyl 2-oxo-3-phenylsuccinate, Na salt. Subsequent reaction with formaldehyde in the presence of potassium carbonate results in ethyl atropate with a methyl ester content not exceeding 0.05%.

Provenance & Evidence