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

HRID 2053404Notes

Reaction equation

[CH:1]1[C:6]([C:7]2[C:16](=O)[C:15]3C(O)=CC(O)=CC=3OC=2)=[CH:5][CH:4]=[C:3](O)[CH:2]=1.[OH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:29].C(OCC)(=O)C=CC1C=CC=CC=1>>[C:6]1([CH:7]=[CH:16][C:15]2[O:21][C:22]3[C:23]([C:28](=[O:29])[C:30]=2[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:1]=[CH:2][CH:3]=[CH:4][CH:5]=1

Participants

Reactant 3

HCID 7649Ethyl 3-phenylprop-2-enoate

HCID 137612Acetophenone, 2'-hydroxy-2-phenyl-

HCID 5280961Genistein

Product 1

HCID 69288434HCID 69288434, compound

Procedure

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.

Sources & evidence

ORD record: ord-bd45aa9d94434eeaad5a5bfa0c0af5dd
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07326797B2

Reaction notes

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