Ethyl 3-phenylprop-2-enoate → HCID 69288434, compound

Participants

Reaction Steps

In the earlier years, from about 1928 to about 1952, two synthetic routes to genistein and related isoflavones were predominantly available. The first route involved the reaction of a 2-hydroxydeoxybenzoin with a cinnamic acid ester, e.g. ethyl cinnamate, to afford the corresponding 2-(2-phenylethenyl)-isoflavone, followed by oxidation with potassium permanganate and thermal decarboxylation to the isoflavanone compound: see W. Baker et al., J. Chem. Soc. 1926, 2713; ibid. 1928, 3115; and ibid. 1933, 274. The second route involved the reaction of a 2-hydroxydeoxybenzoin with sodium and ethyl formate to produce the appropriate 2H-isoflavone compound directly: see H. S. Mahal et al., J. Chem. Soc. 1934, 1769; F. Wessely et al., Chem. Ber. 66, 685 (1933); and R. L. Shriner, J. Org. Chem. 10, 288 (1945). Both routes in whatever variation led to inadequate yields of the desired isoflavone compound.

Provenance & Evidence