2,6-Dichlorobenzoyl chloride → 2,6-Dichloro-3',4'-dimethoxy-2'-hydroxy-6'-methylbenzophenone

HRID 361965

Reaktionsgleichung

[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:7]=1[C:8](Cl)=[O:9].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH3:28])[CH:21]=[C:22]([O:26]C)[C:23]=1[O:24][CH3:25]>ClCCl>[Cl:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:7]=1[C:8]([C:21]1[C:20]([CH3:28])=[CH:19][C:18]([O:17][CH3:16])=[C:23]([O:24][CH3:25])[C:22]=1[OH:26])=[O:9]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Aluminum chloride (14.67 g, 0.1 mol), 2,6-dichlorobenzoyl chloride (20.95 g, 0.1 mol) and a solution of 3,4,5-trimethoxytoluene (18.22 g, 0.1 mol) in dichloromethane (50 ml), are slowly and consecutively added to dichloromethane stirred at 0° C., stirred for 1 h at ice bath temperatures and for 16 h at room temperature, and poured into ice. The organic layer is separated, washed with dilute hydrochloric acid and water, dried, and, after addition of silica gel (100 g), concentrated in vacuo. A flash chromatography column is packed with silica gel (400 g) andthe charged silica gel is layered on top of that. Elution with petrol ether/ethyl acetate (90/10, 1 l; 80/20, 1 l; 50/50, 1 l) yields 2,6-dichloro-3',4'-dimethoxy-2'-hydroxy-6'-methylbenzophenone, 10.35 g, (30% y), mp. 161° C.

Aufarbeitung

stirringstirred for 1 h at ice bath temperatures
additionpoured into ice
customThe organic layer is separated
washwashed with dilute hydrochloric acid and water
customdried
additionafter addition of silica gel (100 g)
concentrationconcentrated in vacuo
washElution with petrol ether/ethyl acetate (90/10, 1 l; 80/20, 1 l; 50/50, 1 l)

Quellen und Nachweise

ORD-Eintrag: ord-d73ccbad4d6e4cc99abbd33baaaf8750
Quelldatensatz: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05866722

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