Veratrole → 3,4-Dimethoxybenzophenone

HRID 583439

Reaktionsgleichung

Reaktionsgleichung von HRID 583439
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, 7H), 6.95-6.85 (m, 1H), 3.96 (s, 3H), 3.94 (s, 3H); 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-d42586159a8841cca8f416680f3f499c
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05929117

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