4'-CHLORO-3-PHENYLPROPIOPHENONE

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: p-chlorophenyl phenylethyl ketone (25 g) was refluxed with hydrazine hydrate (13 g) and potassium hydroxide (18 g) in Digol (diethylene glycol) for one hour. The mixture was then distilled until the solution temperature in the still reached 175°. The mixture was then refluxed for 3 hours, cooled, poured into water and extracted with petroleum ether (Bpt 40°-60°). Evaporation of the extracts gave 1-(4-chlorophenyl)-3-phenylpropane Bbt. 110°/10-3 mm. The mixture was then distilled until the solution temperature in the still reached 175° The mixture was then refluxed for 3 hours cooled poured into water extracted with petroleum ether (Bpt 40°-60°) Evaporation of the extracts

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylpropionyl chloride (33.7 g) in benzene was added dropwise to a stirred mixture of 4-chlorophenyl magnesium bromide (derived from 38 g of 4-chlorobromobenzene) and cadmium chloride (37 g) in benzene at 0°. The mixture was stirred at room temperature for 6 hours and aqueous ammonium chloride solution then added. Ether extraction yielded p-chlorophenyl phenylethyl ketone (25 g) m.p. 78°-79°. Ether extraction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: p-chlorophenyl phenylethyl ketone (25 g) was refluxed with hydrazine hydrate (13 g) and potassium hydroxide (18 g) in Digol (diethylene glycol) for one hour. The mixture was then distilled until the solution temperature in the still reached 175°. The mixture was then refluxed for 3 hours, cooled, poured into water and extracted with petroleum ether (Bpt 40°-60°). Evaporation of the extracts gave 1-(4-chlorophenyl)-3-phenylpropane Bbt. 110°/10-3 mm. The mixture was then distilled until the solution temperature in the still reached 175° The mixture was then refluxed for 3 hours cooled poured into water extracted with petroleum ether (Bpt 40°-60°) Evaporation of the extracts

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylpropionyl chloride (33.7 g) in benzene was added dropwise to a stirred mixture of 4-chlorophenyl magnesium bromide (derived from 38 g of 4-chlorobromobenzene) and cadmium chloride (37 g) in benzene at 0°. The mixture was stirred at room temperature for 6 hours and aqueous ammonium chloride solution then added. Ether extraction yielded p-chlorophenyl phenylethyl ketone (25 g) m.p. 78°-79°. Ether extraction