Hydrochloric Acid → Chrysin

HRID 272104Notes

Reaction equation

HRID 272104 reaction equation
C(OP(CC=CCOC1C=CC=CC=1C(Cl)=O)(=O)OCC)C.[H-].[Na+].Cl.C(=O)([O-])[O-].[Na+].[Na+].C[O:33][C:34]1[CH:43]=[C:42]([O:44]C)[CH:41]=[C:40]2[C:35]=1[C:36](=[O:52])[CH:37]=[C:38]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[O:39]2>>[OH:33][C:34]1[CH:43]=[C:42]([OH:44])[CH:41]=[C:40]2[C:35]=1[C:36](=[O:52])[CH:37]=[C:38]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[O:39]2

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 888815,7-DimethoxyflavoneHCID 72557682HCID 72557682, compound

Product 1

HCID 5281607Chrysin

Procedure

Condensation with [4-(2-chlorocarbonyl-phenoxy)-but-2-enyl]-phosphonic acid diethyl ester (synthesis below) is followed by successive treatment with sodium hydride, hydrochloric acid and sodium carbonate, generating the 5,7-dimethoxyflavone. Demethylation to provide the 5,7-dihydroxyflavone final product is achieved as in Scheme 27.2 (see Bioorg. Med. Chem. Lett., (2000), 10, 1037).

Sources & evidence

ORD record
ord-cde793510ed54f1cb3e10ba7b305f589
Source dataset
uspto-grants-2008_11
Patent number
US07452901B2

Reaction notes

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