Ethyl propiolate → HCID 178491959, compound

Participants

Reaction Steps

A solution of 72.7 g of 4-methoxyphenylhydrazine in 700 ml of tert-butanol was treated dropwise at 30° C. with 56.8 g of ethyl propiolate. A total of 118 g of potassium tert-butoxide was then introduced in portions with ice cooling into the mixture thus obtained. After 12 h at 25° C., the solvent was distilled off under reduced pressure and the residue thus obtained was taken up in water. The aqueous solution was washed with dichloromethane and then acidified with conc. acetic acid with cooling to a pH of 9, the product being deposited as a solid. After washing and drying, 60.3 g of the title compound (60% of theory) were obtained; m.p.: 167°-170° C.

Provenance & Evidence