2-Acetylhydroquinone → 2-(3-Chlorophenyl)-6-hydroxychroman-4-one

HRID 31183

Reaktionsgleichung

Reaktionsgleichung von HRID 31183
F[C:2]1[CH:3]=[C:4]([CH:8]2[CH2:17][C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:19])[CH:14]=3)[O:9]2)[CH:5]=[CH:6][CH:7]=1.OC1C=CC(O)=CC=1C(=O)C.[Cl:31]C1C=C(C=CC=1)C=O>>[Cl:31][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:17][C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:19])[CH:14]=3)[O:9]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 102792-AcetylhydroquinoneHCID 114773-ChlorobenzaldehydeHCID 179784652-(3-Fluorophenyl)-6-hydroxychroman-4-one

Produkt 1

HCID 179784992-(3-Chlorophenyl)-6-hydroxychroman-4-one

Versuchsvorschrift

2-(3-Chlorophenyl)-6-hydroxychroman-4-one was prepared as described for 2-(3-fluorophenyl)-6-hydroxychroman-4-one in Example 9(a) starting from 2.0 g of 2′,5′-dihydroxyacetophenone and 1.85 g of 3-chlorobenzaldehyde. The product was recrystallised from acetic acid. 1H NMR (400 MHz, d6-DMSO) δ: 9.47 (s, 1H), 7.62 (s, 1H), 7.51-7.45 (m, 3H), 7.12 (d, 1H, J 3.0 Hz), 7.05 (dd, 1H, J 8.8, 3.0 Hz), 6.98 (d, 1H, J 8.8 Hz), 5.58 (dd, 1H, J 13.1, 2.9 Hz), 3.18 (dd, 1H, J −16.9, 13.1 Hz), 2.81 (dd, 1H, J −16.9, 2.9 Hz).

Aufarbeitung

  1. customThe product was recrystallised from acetic acid

Quellen und Nachweise

ORD-Eintrag
ord-20abb66112f84691b5747087983e523d
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425568B2

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