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Diphenyldichloromethane

Diphenyldichloromethane is an organic compound with the formula (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>CCl<sub>2</sub>. It is a colorless solid that is used as a precursor to other organic compounds.

Synthesis

It is prepared from carbon tetrachloride and anhydrous aluminium chloride as catalyst in a double Friedel-Crafts alkylation of benzene. Alternatively, benzophenone is treated with phosphorus pentachloride:

(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>CO + PCl<sub>5</sub> → (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>CCl<sub>2</sub> + POCl<sub>3</sub>

Reactions

It undergoes hydrolysis to benzophenone.

(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>CCl<sub>2</sub> + H<sub>2</sub>O → (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>CO + 2 HCl

Reductive dehalogenation of diphenyldichloromethane with copper or with nickel gives tetraphenylethylene:

References