Diethyl Ether → 1-[1-(3,4-Dichlorophenyl)cyclopentyl]ethanone

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Reaction Steps

Methylmagnesium iodide (3M solution in ether; 100 ml) was added dropwise at 0° C. under nitrogen to a stirred solution of 1-(3,4-dichlorophenyl)cyclopentanecarbonitrile (48 g) in ether (100 ml), then the mixture was stirred at ambient temperature for 24 hours. The resulting solid was collected by filtration, washed well with ether, and added in portions to an ice-cold mixture of water (200 ml) and concentrated hydrochloric acid (125 ml). The mixture was heated at 95° C. with occasional stirring for 1 hour, then it was allowed to cool to ambient temperature. The product was extracted into ether (5×100 ml), then the combined extracts were washed with water (2×100 ml), dried (MgSO4), and the solvent was removed in vacuo. The residue was distilled to give 1-[1-(3,4-dichlorophenyl)cyclopentyl]ethanone as a pale yellow oil (31.9 g), b.p. 124-128° C/0.5 mbar.

Provenance & Evidence