5-(2-(4-Hydroxyphenyl)Ethenyl)Benzene-1,3-Diol → 5-(2-(4-Hydroxyphenyl)Ethenyl)Benzene-1,3-Diol

HRID 1163265

Reaktionsgleichung

Reaktionsgleichung von HRID 1163265
[C:1]1([CH:9]=[CH:10][C:11]2[CH:17]=[CH:16][C:14]([OH:15])=[CH:13][CH:12]=2)[CH:8]=[C:6]([OH:7])[CH:5]=[C:3]([OH:4])[CH:2]=1.[OH:18]C1C=C(C=C(O)C=1)C=O.OC1C=C(C=C(O)C=1)C=C.C(OC1C=CC(I)=CC=1)(=O)C>>[C:1]1([CH:9]=[CH:10][C:11]2[CH:17]=[CH:16][C:14]([OH:15])=[CH:13][CH:12]=2)[CH:8]=[C:6]([OH:7])[CH:5]=[C:3]([OH:4])[CH:2]=1.[CH:12]1[C:11](/[CH:10]=[CH:9]/[C:1]2[CH:8]=[C:6]([OH:7])[CH:5]=[C:3]([OH:4])[CH:2]=2)=[CH:17][C:16]([OH:18])=[C:14]([OH:15])[CH:13]=1

Komponenten

6

Edukt 4

HCID 50565-(2-(4-Hydroxyphenyl)Ethenyl)Benzene-1,3-Diol2×HCID 943653,5-DihydroxybenzaldehydeHCID 1417934-IodophenylacetateHCID 121640635-Ethenyl-1,3-benzenediol

Produkt 2

HCID 50565-(2-(4-Hydroxyphenyl)Ethenyl)Benzene-1,3-DiolHCID 667639Piceatannol

Versuchsvorschrift

Processes for the preparation of resveratrol have been disclosed, inter alia, in WO 01/60774 and Tetrahedron Letters 43 (2002) 597-598. The latter reference describes a process wherein resveratrol is prepared by a multistep reaction sequence starting with 3,5-dihydroxybenzaldehyde and involving a Heck reaction of 3,5-dihydroxystyrene with 4-acetoxy-iodobenzene in a yield of 70%. The process of the present invention utilizes a more readily available starting material and proceeds in less steps and superior yield, thus providing a technically more attractive approach to resveratrol and piceatannol and derivatives, such as esters, thereof.

Aufarbeitung

  1. customis prepared by a multistep reaction sequence

Quellen und Nachweise

ORD-Eintrag
ord-00134d72c1124357a29b76cff212c850
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820848B2

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