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

HRID 582380Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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) and the 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.

Workup

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 )

Sources & evidence

ORD record: ord-aff068e7512047c88cfb1d3fda64bb8d
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05922919

Reaction notes

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