2-(4-benzylphenyl)acetonitrile

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

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

Procedure: The crude bromomethylbenzene intermediate (19.6 g, 75 mmole) was treated with NaCN as in Example 2 and, after chromatography over silica gel (10 to 100% EtOAc in hexane), 5.2 g (33%) of 4-benzyl-l-cyanomethylbenzene and 1.43 g (9.2%) of 3-benzyl-1-cyanomethylbenzene were obtained, both as oils.

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

Procedure: To a suspention of sodium methoxide (64.26 g) in toluene (2.5 l) was added dropwise at 0° C. a mixture of ethyl formate (88.14 g) and 4-benzylphenylacetonitrile (189.69 g) with stirring. After 30 minutes, ice bath was removed. After 20 hours, ice water (2.6 l) was added to the reaction mixture, and the aqueous layer was separated. The organic layer was washed with 0.5N sodium hydroxide aqueous solution (500 ml×5). The aqueous layer and the washings were combined, adjusted to acid with conc. hydrochloric acid, and stirred at 0° C. for 30 minutes. The precipitate was separated by filtration, washed, and dried to give the title compound (152.22 g). ice bath was removed After 20 hours ice water (2.6 l) was added to the reaction mixture the aqueous layer was separated The organic layer was washed with 0.5N sodium hydroxide aqueous solution (500 ml×5) stirred at 0° C. for 30 minutes The precipitate was separated by filtration washed dried

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

Procedure: To a solution of 4-benzylbenzyl chloride (198.34 g) in dimethylchloride (DMF) (50 ml) was added in turn sodium hydrogen carbonate (76.88 g) and sodium cyanide (56.07 g). In that case, the solution was cooled as occasion demands, since heat is slightly generated. After stirring at room temperature for 17 hours, DMF (100 ml) was further added. After stirring at room temperature for 67 hours, ethyl acetate (300 ml) was added, and the precipitate was filtered, washed with ethyl acetate (300 ml). The filtrate and the washings were combined, washed with saturated aqueouse sodium chloride solution (20 ml×4), dried over anhydrous sodium sulfate, concentrated under reduced pressure to give the title compound (189.69 g). In that case, the solution was cooled as occasion demands since heat After stirring at room temperature for 67 hours the precipitate was filtered washed with ethyl acetate (300 ml) washed with saturated aqueouse sodium chloride solution (20 ml×4) dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: The crude bromomethylbenzene intermediate (19.6 g, 75 mmole) was treated with NaCN as in Example 2 and, after chromatography over silica gel (10 to 100% EtOAc in hexane), 5.2 g (33%) of 4-benzyl-l-cyanomethylbenzene and 1.43 g (9.2%) of 3-benzyl-1-cyanomethylbenzene were obtained, both as oils.

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

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

Procedure: To a suspention of sodium methoxide (64.26 g) in toluene (2.5 l) was added dropwise at 0° C. a mixture of ethyl formate (88.14 g) and 4-benzylphenylacetonitrile (189.69 g) with stirring. After 30 minutes, ice bath was removed. After 20 hours, ice water (2.6 l) was added to the reaction mixture, and the aqueous layer was separated. The organic layer was washed with 0.5N sodium hydroxide aqueous solution (500 ml×5). The aqueous layer and the washings were combined, adjusted to acid with conc. hydrochloric acid, and stirred at 0° C. for 30 minutes. The precipitate was separated by filtration, washed, and dried to give the title compound.(152.22 g). ice bath was removed After 20 hours ice water (2.6 l) was added to the reaction mixture the aqueous layer was separated The organic layer was washed with 0.5N sodium hydroxide aqueous solution (500 ml×5) stirred at 0° C. for 30 minutes The precipitate was separated by filtration washed dried

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

Procedure: To a solution of 4-benzylbenzyl chloride (198.34 g) in dimethylchloride (DMF) (50 ml) was added in turn sodium hydrogen carbonate (76.88 g) and sodium cyanide (56.07 g). In that case, the solution was cooled as occasion demands, since heat is slightly generated. After stirring at room temperature for 17 hours, DMF (100 ml) was further added. After stirring at room temperature for 67 hours, ethyl acetate (300 ml) was added, and the precipitate was filtered, washed with ethyl acetate (300 ml). The filtrate and the washings were combined, washed with saturated aqueouse sodium chloride solution (20 ml×4), dried over anhydrous sodium sulfate, concentrated under reduced pressure to give the title compound (189.69 g). In that case, the solution was cooled as occasion demands since heat After stirring at room temperature for 67 hours the precipitate was filtered washed with ethyl acetate (300 ml) washed with saturated aqueouse sodium chloride solution (20 ml×4) dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: To a suspention of sodium methoxide (64.26 g) in toluene (2.5 l) was added dropwise at 0° C. a mixture of ethyl formate (88.14 g) and 4-benzylphenylacetonitrile (189.69 g) with stirring. After 30 minutes, ice bath was removed. After 20 hours, ice water (2.6 l) was added to the reaction mixture, and the aqueous layer was separated. The organic layer was washed with 0.5N sodium hydroxide aqueous solution (500 ml×5). The aqueous layer and the washings were combined, adjusted to acid with conc. hydrochloric acid, and stirred at 0° C. for 30 minutes. The precipitate was separated by filtration, washed, and dried to give the title compound (152.22 g). ice bath was removed After 20 hours ice water (2.6 l) was added to the reaction mixture the aqueous layer was separated The organic layer was washed with 0.5N sodium hydroxide aqueous solution (500 ml×5) stirred at 0° C. for 30 minutes The precipitate was separated by filtration washed dried

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

Procedure: To a solution of 4-benzylbenzyl chloride (198.34 g) in dimethylchloride (DMF) (50 ml) was added in turn sodium hydrogen carbonate (76.88 g) and sodium cyanide (56.07 g). In that case, the solution was cooled as occasion demands, since heat is slightly generated. After stirring at room temperature for 17 hours, DMF (100 ml) was further added. After stirring at room temperature for 67 hours, ethyl acetate (300 ml) was added, and the precipitate was filtered, washed with ethyl acetate (300 ml). The filtrate and the washings were combined, washed with saturated aqueouse sodium chloride solution (20 ml×4), dried over anhydrous sodium sulfate, concentrated under reduced pressure to give the title compound (189.69 g). In that case, the solution was cooled as occasion demands since heat After stirring at room temperature for 67 hours the precipitate was filtered washed with ethyl acetate (300 ml) washed with saturated aqueouse sodium chloride solution (20 ml×4) dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: The crude bromomethylbenzene intermediate (19.6 g, 75 mmole) was treated with NaCN as in Example 2 and, after chromatography over silica gel (10 to 100% EtOAc in hexane), 5.2 g (33%) of 4-benzyl-l-cyanomethylbenzene and 1.43 g (9.2%) of 3-benzyl-1-cyanomethylbenzene were obtained, both as oils.