Veratrole → (3,4-Dimethoxyphenyl)(3,5-dimethoxyphenyl)methanone

HRID 971025

Reaktionsgleichung

Reaktionsgleichung von HRID 971025
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:6](Cl)=[O:7].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23].[Cl-].[Al+3].[Cl-].[Cl-].COC1C=C(C(C2C=CC(OC)=CC=2)=CC#N)C=CC=1OC>>[CH3:14][O:15][C:16]1[CH:21]=[C:20]([C:6]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=2)=[O:7])[CH:19]=[CH:18][C:17]=1[O:22][CH3:23]

Komponenten

5

Edukt 4

HCID 7043VeratroleHCID 870033,5-Dimethoxybenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 692026013-(3,4-Dimethoxy-phenyl)-3-(4-methoxy-phenyl)-acrylonitrile

Produkt 1

HCID 21584591(3,4-Dimethoxyphenyl)(3,5-dimethoxyphenyl)methanoneAusbeute 72 %

Versuchsvorschrift

3,5-Dimethoxybenzoyl chloride (10.28 g, 51.24 mmol), 1,2-dimethoxybenzene (6.53 ml, 51.24 mmol), and aluminum chloride (7.52 g, 56.37 mmol) were treated in the same manner as described above for the synthesis of 3-(3,4-dimethoxy-phenyl)-3-(4-methoxy-phenyl)-acrylonitrile. The crude was purified via flash column chromatography (10% EtOAc in hexane gradient to 50% EtOAc in hexane in 50 min.) to give (3,4-dimethoxy-phenyl)-(3,5-dimethoxy-phenyl)-methanone as a light yellow solid (11.14 g, 72%); 1HNMR (DMSO-d6) δ 7.38-7.33 (m, 2H, Ar), 7.09 (d, J=8 Hz, 1H, Ar), 6.77 (s, 3H, OCH3), 3.86 (s, 3H, OCH3), 3.82 (s, 3H, OCH3), 3.79 (s, 6H, 2OCH3). The product was carried over to the next step.

Aufarbeitung

  1. customThe crude was purified via flash column chromatography (10% EtOAc in hexane gradient to 50% EtOAc in hexane in 50 min.)

Quellen und Nachweise

ORD-Eintrag
ord-81aa1eca28a540b2841e917f89a3ddb6
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312241B2

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