1-[4-(2-phenylethyl)phenyl]ethanone

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of 87.5 g (0.39 mole) of 4'-phenethylacetophenone, M.P. 67°-70° C., prepared according to R. E. Lutz et al., J. Org. Chem. 12, 617 (1947), and 98.5 g (1.56 mole) of ammonium formate is slowly heated to 150° C. with stirring. After the initial foaming has subsided the temperature of the heating bath is raised to 185°-190° C. for a period of 4 hours. Upon cooling, the mixture is treated with several portions of water. To the residue is added 75 ml of concentrated HCl. The mixture is refluxed for 2 hours and is allowed to cool. The resulting solid is collected, washed with several portions of benzene and is recrystallized from isopropanol containing about 5% of water to yield 74.0 g (73% yield) of the desired product, M.P. 212°-214° C. prepared is raised to 185°-190° C. for a period of 4 hours Upon cooling The mixture is refluxed for 2 hours to cool The resulting solid is collected washed with several portions of benzene is recrystallized from isopropanol containing about 5% of water

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

Procedure: A mixture of 87.5 g (0.39 mole) of 4'-phenethylacetophenone, M.P. 67°-70° C., prepared according to R. E. Lutz et al., J. Org. Chem. 12, 617 (1947), and 98.5 g (1.56 mole) of ammonium formate is slowly heated to 150° C. with stirring. After the initial foaming has subsided the temperature of the heating bath is raised to 185°-190° C. for a period of 4 hours. Upon cooling, the mixture is treated with several portions of water. To the residue is added 75 ml of concentrated HCl. The mixture is refluxed for 2 hours and is allowed to cool. The resulting solid is collected, washed with several portions of benzene and is recrystallized from isopropanol containing about 5% of water to yield 74.0 g (73% yield) of the desired product, M.P. 212°-214° C. prepared is raised to 185°-190° C. for a period of 4 hours Upon cooling The mixture is refluxed for 2 hours to cool The resulting solid is collected washed with several portions of benzene is recrystallized from isopropanol containing about 5% of water

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Magnesium methyl carbonate (0.4 mole, 2 M in dimethylformamide) is heated to 120°C. under carbon dioxide. The compound 4'-phenethylacetophenone, 22.4 g (0.1 mole), is added and the mixture is stirred at 120°C. for 4 hours under a stream of nitrogen allowing the methanol that forms to escape. The reaction mixture is allowed to cool to room temperature under an atmosphere of carbon dioxide and 8.3 g (0.12 mole) of 1-pyrroline (as the trimer) added and stirred at room temperature under carbon dioxide for a period of 40 hours. The solution is poured into a mixture of 200 ml of concentrated HCl and 800 g of ice and the product removed by filtration. The 4'-phenethyl-2-(2-pyrrolidinyl)-acetophenone when twice recrystallized in the form of its hydrochloride salt from an aqueous isopropanol solution is obtained in 63% yield (20.1 g) and has a M.P. of 200-1°C. (dec). the product removed by filtration The 4'-phenethyl-2-(2-pyrrolidinyl)-acetophenone when twice recrystallized in the form of its hydrochloride salt from an aqueous isopropanol solution is obtained in 63% yield (20.1 g)

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

Procedure: A mixture of 87.5 g (0.39 mole) of 4'-phenethylacetophenone, M.P. 67°-70° C., prepared according to R. E. Lutz et al., J. Org. Chem. 12, 617 (1947), and 98.5 g (1.56 mole) of ammonium formate is slowly heated to 150° C. with stirring. After the initial foaming has subsided the temperature of the heating bath is raised to 185°-190° C. for a period of 4 hours. Upon cooling, the mixture is treated with several portions of water. To the residue is added 75 ml of concentrated HCl. The mixture is refluxed for 2 hours and is allowed to cool. The resulting solid is collected, washed with several portions of benzene and is recrystallized from isopropanol containing about 5% of water to yield 74.0 g (73% yield) of the desired product, M.P. 212°-214° C. prepared is raised to 185°-190° C. for a period of 4 hours Upon cooling The mixture is refluxed for 2 hours to cool The resulting solid is collected washed with several portions of benzene is recrystallized from isopropanol containing about 5% of water

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

Procedure: A mixture of 87.5 g (0.39 mole) of 4'-phenethylacetophenone, M.P. 67°-70° C., prepared according to R. E. Lutz et al., J. Org. Chem. 12, 617 (1947), and 98.5 g (1.56 mole) of ammonium formate is slowly heated to 150° C. with stirring. After the initial foaming has subsided the temperature of the heating bath is raised to 185°-190° C. for a period of 4 hours. Upon cooling, the mixture is treated with several portions of water. To the residue is added 75 ml of concentrated HCl. The mixture is refluxed for 2 hours and is allowed to cool. The resulting solid is collected, washed with several portions of benzene and is recrystallized from isopropanol containing about 5% of water to yield 74.0 g (73% yield) of the desired product, M.P. 212°-214° C. prepared is raised to 185°-190° C. for a period of 4 hours Upon cooling The mixture is refluxed for 2 hours to cool The resulting solid is collected washed with several portions of benzene is recrystallized from isopropanol containing about 5% of water