2-Acetylhydroquinone → 2-(2,4-Dichlorophenyl)-6-hydroxychroman-4-one

HRID 31179

Reaktionsgleichung

Reaktionsgleichung von HRID 31179
FC1C=C(C2CC(=O)C3C(=CC=C(O)C=3)O2)C=CC=1.[OH:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=1[C:28](=[O:30])[CH3:29].[Cl:31][C:32]1[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:33]=1[CH:34]=O>>[Cl:31][C:32]1[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:33]=1[CH:34]1[CH2:29][C:28](=[O:30])[C:22]2[C:21](=[CH:26][CH:25]=[C:24]([OH:27])[CH:23]=2)[O:20]1

Komponenten

4

Edukt 3

HCID 102792-AcetylhydroquinoneHCID 134042,4-DichlorobenzaldehydeHCID 179784652-(3-Fluorophenyl)-6-hydroxychroman-4-one

Produkt 1

HCID 179785862-(2,4-Dichlorophenyl)-6-hydroxychroman-4-one

Versuchsvorschrift

2-(2,4-Dichlorophenyl)-6-hydroxychroman-4-one was prepared as described for 2-(3-fluorophenyl)-6-hydroxychroman-4-one in Example 9(a) starting from 1.0 g of 2′,5′-dihydroxyacetophenone and 1.4 g of 2,4-dichlorobenzaldehyde. The product was recrystallised from acetic acid. 1H NMR (400 MHz, d6-DMSO) δ: 9.49 (s, 1H), 7.78 (d, 1H, J 8.5 Hz), 7.71(d, 1H, J 2.0 Hz), 7.57 (dd, 1H, J 8.5, 2.0 Hz), 7.14 (d, 1H, J 3.0 Hz), 7.06 (dd, 1H, J 8.8, 3.0 Hz), 6.97 (d, 1H, J 8.8 Hz), 5.77 (dd, 1H, J 13.5, 2.7 Hz), 3.18 (dd, 1H, J −16.9, 13.5 Hz), 2.78 (dd, 1H, J −16.9, 2.7 Hz).

Aufarbeitung

  1. customThe product was recrystallised from acetic acid

Quellen und Nachweise

ORD-Eintrag
ord-aabe3698b6c642ef8b305a4a22d81402
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425568B2

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