Veratrole → Methanone, (3,4-dimethoxyphenyl)(3-methoxyphenyl)-

HRID 971021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 971021
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21].[Cl-].[Al+3].[Cl-].[Cl-].COC1C=C(C(C2C=CC(OC)=CC=2)=CC#N)C=CC=1OC>C(Cl)Cl>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([C:6]([C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:7])[CH:17]=[CH:16][C:15]=1[O:20][CH3:21]

Komponenten

6

Edukt 4

HCID 7043VeratroleHCID 74374m-Anisoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 692026013-(3,4-Dimethoxy-phenyl)-3-(4-methoxy-phenyl)-acrylonitrile

Produkt 1

HCID 11032987Methanone, (3,4-dimethoxyphenyl)(3-methoxyphenyl)-Ausbeute 110 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-methoxybenzoyl chloride (2.06 ml, 14.65 mmol), 1,2-dimethoxybenzene (1.87 ml, 14.65 mmol) in anhydrous methylene chloride (25 ml), and aluminum chloride (2.15 g, 16.12 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 (20% EtOAc in hexane) to give (3,4-dimethoxy-phenyl)-(3-methoxy-phenyl)-methanone as a yellow oil (4.39 g, 100%); 1HNMR (CDCl3) δ 7.50 (d, J=1 Hz, 1H, Ar), 7.42-7.30 (m, 4H, Ar), 7.14-7.09 (m, 1H, Ar), 6.90 (d, J=8 Hz, 1H, Ar), 3.96 (s, 3H, OCH3), 3.95 (s, 6H, 2OCH3), 3.86 (s, 3H, OCH3); 13C NMR (CDCl3) δ 195.4, 159.6, 153.1, 149.1, 139.7, 130.3, 129.2, 125.6, 122.5, 118.3, 114.4, 112.3, 109.9, 56.2, 56.2, 55.6; Anal. Calcd. For C16H16O4: C, 70.58; H, 5.92. Found: C, 70.38; H, 5.99; N, <0.05. The product was carried over to the next step.

Aufarbeitung

  1. customThe crude was purified via flash column chromatography (20% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-359c4c2174fa44a797dfaacf8605a4c6
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312241B2

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