Benzoyl chloride → HCID 605605, compound

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Reaction Steps

To 100 ml. of methylene chloride is added 50 g. of dry aluminum chloride. The mixture is stirred and 28 g. of benzoyl chloride is added dropwise. While the solution is stirred at 30°-40°C, 16.4 g. of methyl β-phenylpropionate is added dropwise over a period of about 1 hour. After the drop-by-drop addition has been completed, the solution is stirred at 30°-40°C for 2 hours. After cooling, the solution is poured into ice-hydrochloric acid and extracted with methylene chloride. The extract is washed with dilute hydrochloric acid, water, dilute aqueous sodium hydroxide and water in the order mentioned, followed by drying. The solvent is distilled off under reduced pressure and the residue is purified by column chromatography (1 kg. of silica gel; eluted with benzene). The described procedure gives methyl p-benzoyl-β-phenylpropionate and methyl o-benzoyl-β-phenylpropionate.

Provenance & Evidence