Veratrole → 3,4-Dimethoxybenzophenone

HRID 1017921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1017921
CO[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1OC)[C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)=[O:7].C1(OC)C(=CC=CC=1)OC.[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)(=O)C1C=CC=CC=1>>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][C:11]=1[O:14][CH3:15])[C:6]([C:5]1[CH:18]=[CH:19][CH:20]=[CH:3][CH:4]=1)=[O:7]

Komponenten

5

Edukt 4

HCID 7043VeratroleHCID 7412Benzoyl chlorideHCID 223042Bis(3,4-dimethoxyphenyl)methanoneHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 2867423,4-Dimethoxybenzophenone

Versuchsvorschrift

3,4-Dimethoxybenzophenone was prepared analogously to 3,4,3′,4′-tetramethoxybenzophenone using veratrole (2 mL, 15 mmol), aluminum chloride (2.2 g, 16.5 mmol) and benzoyl chloride (1.8 mL, 15.5 mmol). The crude mixture was purified by flash column chromatography (silica gel, 3% ethyl acetate/methylene chloride) to yield 3.44 g (93%) of the product as a white solid: mp 99-100° C.; 1H NMR (CDCl3) δ 7.82-7.30 (m, 7 H), 6.95-6.85 (m, 1 H), 3.96 (s, 3 H), 3.94 (s, 3 H); 13C NMR (CDCl3) δ 195.5, 153.0, 149.0, 138.2, 131.8, 130.2, 129.6, 128.1, 125.4, 112.1, 109.7, 56.0, 56.0; Anal. Calcd for C15H14O3. Theoretical: C, 74.36; H, 5.82. Found: C, 74.21; H, 6.01.

Aufarbeitung

  1. customThe crude mixture was purified by flash column chromatography (silica gel, 3% ethyl acetate/methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-ca526c6989264faa957ade5d6a0a1564
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479554B2

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