1,2-Diethylbenzene → 3',4'-Diethyl-3,4-dimethoxybenzophenone

HRID 366631

Reaktionsgleichung

Reaktionsgleichung von HRID 366631
C(C1C=C(C=CC=1CC)C(C1C=CC=CC=1)=O)C.[CH2:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][CH3:28])[CH3:20].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:33][O:34][C:35]1[CH:36]=[C:37]([CH:41]=[CH:42][C:43]=1[O:44][CH3:45])[C:38](Cl)=[O:39]>>[CH2:19]([C:21]1[CH:26]=[C:25]([C:38](=[O:39])[C:37]2[CH:41]=[CH:42][C:43]([O:44][CH3:45])=[C:35]([O:34][CH3:33])[CH:36]=2)[CH:24]=[CH:23][C:22]=1[CH2:27][CH3:28])[CH3:20]

Komponenten

5

Edukt 4

HCID 86571,2-DiethylbenzeneHCID 77070Veratroyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 215845983,4-Diethylbenzophenone

Produkt 1

HCID 215846043',4'-Diethyl-3,4-dimethoxybenzophenone

Versuchsvorschrift

3',4'-Diethyl-3,4-dimethoxybenzophenone was prepared analogously to 3,4-diethylbenzophenone using diethylbenzene (2.5 mL, 15 mmol), aluminum chloride (2.2 g, 16.5 mmol) and 3,4-dimethoxybenzoyl chloride (3 g, 15 mmol) with a reaction time of 3 hours at reflux. The crude product was purified by flash column chromatography (silica gel, 1.5% ethyl acetate/hexane) to afford 0.84 g (20%) of the product as an orange solid: mp 60-61° C.; 1H NMR (CDCl3) δ 7.74-7.15 (m, 5 H), 7.00-6.80 (m, 1 H) 3.96 (s, 3 H), 3.94 (s, 3 H), 2.93-2.60 (m, 4 H), 1.43-1.15 (m, 6 H); 13C NMR (CDCl3) δ 195.5, 152.7, 148.8, 146.3, 141.7, 135.9, 130.6, 129.8, 128.0, 127.7, 125.1, 112.2, 109.7, 56.0, 25.6, 25.4, 15.1, 15.0; Anal. Calcd for C19H22O3. Theoretical: C, 76.48; H, 7.43. Found: C, 76.53; H, 7.34.

Aufarbeitung

  1. customwith a reaction time of 3 hours
  2. temperatureat reflux
  3. customThe crude product was purified by flash column chromatography (silica gel, 1.5% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7c897b0430084398801fef7289a203bf
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130226

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