1,2-Dichloroethane → 1,1'-(9,10-Dihydrophenanthrene-2,7-diyl)bis(2-chloroethanone)

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-chloroacetyl chloride (1.765 mL, 22.19 mmol) and aluminum trichloride (2.96 g, 22.19 mmol) in 1,2-dichloroethane (DCE) (20 mL), 9,10-dihydrophenanthrene (1 g, 5.55 mmol) in 1,2-dichloroethane (DCE) (20 mL) was added dropwise over 5 min at r.t. and the reaction mixture was stirred for 1 h at r.t. and 1 h at 60° C. The reaction mixture was cooled to r.t. then added to a mixture of methanol (50 mL) and H2O (50 mL) and chilled to −5° C. The slurry was warmed to ambient, stirred for 30-60 min and the solids collected. The solids were washed well with H2O and dried at 50-60° C. to constant weight.

Provenance & Evidence