2-(4-hydroxyphenyl)propanenitrile

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

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

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

Procedure: To a solution of 4-hydroxyphenylpropanenitrile (5.25 g) in N,N-dimethyl formamide (40 mL), 3-phenylpropyl bromide (7.1 g) and potassium carbonate (14.79 g) were added, followed by stirring at room temperature for 16 hours. Then, the reaction mixture was diluted with diethyl ether and an organic layer was successively washed with water and brine. After the organic layer was dried, the solvent was concentrated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give the title compound (8.54 g) having the following physical properties. an organic layer was successively washed with water and brine After the organic layer was dried the solvent was concentrated the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

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

Procedure: To a solution of 4-hydroxyphenylpropanenitrile (5.25 g) in N,N-dimethyl formamide (40 mL), 3-phenylpropyl bromide (7.1 g) and potassium carbonate (14.79 g) were added, followed by stirring at room temperature for 16 hours. Then, the reaction mixture was diluted with diethyl ether and an organic layer was successively washed with water and brine. After the organic layer was dried, the solvent was concentrated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give the title compound (8.54 g) having the following physical properties. an organic layer was successively washed with water and brine After the organic layer was dried the solvent was concentrated the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

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

Procedure: To a solution of 4-hydroxyphenylpropanenitrile (5.25 g) in N,N-dimethyl formamide (40 mL), 3-phenylpropyl bromide (7.1 g) and potassium carbonate (14.79 g) were added, followed by stirring at room temperature for 16 hours. Then, the reaction mixture was diluted with diethyl ether and an organic layer was successively washed with water and brine. After the organic layer was dried, the solvent was concentrated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give the title compound (8.54 g) having the following physical properties. an organic layer was successively washed with water and brine After the organic layer was dried the solvent was concentrated the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

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

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

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

Procedure: Finely ground 2-(4-aminophenyl) propionitrile (73 g., 0.5 mole) was suspended in concentrated hydrochloric acid (125 ml.). The stirred suspension was diazotised at 0°-5° C. by the dropwise addition of a solution of sodium nitrite (36.23 g., 0.525 mole) in water (60 ml.) during 1- 2 hours. The almost clear solution was stirred for a further 20 minutes at 5°-10° C., then poured into a stirred, boiling solution of concentrated sulphuric acid (250 ml.) in water (2.5 l.). After 6 minutes it was cooled in an ice-bath, then extracted with ether (×4). The combined ether extracts were extracted with 2N-sodium hydroxide (×6). The combined alkaline extracts were cooled in ice-bath, acidified with concentrated hydrochloric acid and extracted with ether (×3). The combined ether extracts were washed with saturated sodium chloride solution (×3), dried (Na2SO4) and evaporated to leave a dark brown oil (66.7 g.) which on distillation gave 2-(4-hydroxyphenyl) propionitrile (59.58 g.), b.p. 112°-122° C./0.125 m.m., m.p. 41°-46° C. poured into a stirred After 6 minutes it was cooled in an ice-bath extracted with ether (×4) The combined ether extracts were extracted with 2N-sodium hydroxide (×6) The combined alkaline extracts were cooled in ice-bath extracted with ether (×3) The combined ether extracts were washed with saturated sodium chloride solution (×3) dried (Na2SO4) evaporated to leave a dark brown oil (66.7 g.) which on distillation

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

Procedure: Finely ground 2-(4-aminophenyl) propionitrile (73 g., 0.5 mole) was suspended in concentrated hydrochloric acid (125 ml.). The stirred suspension was diazotised at 0°-5° C. by the dropwise addition of a solution of sodium nitrite (36.23 g., 0.525 mole) in water (60 ml.) during 1- 2 hours. The almost clear solution was stirred for a further 20 minutes at 5°-10° C., then poured into a stirred, boiling solution of concentrated sulphuric acid (250 ml.) in water (2.5 l.). After 6 minutes it was cooled in an ice-bath, then extracted with ether (×4). The combined ether extracts were extracted with 2N-sodium hydroxide (×6). The combined alkaline extracts were cooled in ice-bath, acidified with concentrated hydrochloric acid and extracted with ether (×3). The combined ether extracts were washed with saturated sodium chloride solution (×3), dried (Na2SO4) and evaporated to leave a dark brown oil (66.7 g.) which on distillation gave 2-(4-hydroxyphenyl) propionitrile (59.58 g.), b.p. 112°-122° C./0.125 m.m., m.p. 41°-46° C. poured into a stirred After 6 minutes it was cooled in an ice-bath extracted with ether (×4) The combined ether extracts were extracted with 2N-sodium hydroxide (×6) The combined alkaline extracts were cooled in ice-bath extracted with ether (×3) The combined ether extracts were washed with saturated sodium chloride solution (×3) dried (Na2SO4) evaporated to leave a dark brown oil (66.7 g.) which on distillation

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

Procedure: 4-Hydroxy-phenyl-propionitrile is nitrated in glacial acetic acid with 65% strength nitric acid at 10°-15° C, in the course of 2 hours, the 3-nitro-4-hydroxyphenyl-propionitrile (melting point = 104° C) is reduced with hydrogen, using 5% strength palladium charcoal as the catalyst, in ethanol at room temperature to give 3-amino-4-hydroxyphenyl-propionitrile (melting point = 125° C) and the amine compound is acetylated in toluene with molar equivalent amounts of acetic anhydride. The 3-acetamino-4-hydroxyphenyl-propionitrile (melting point = 191°-192°) is slowly warmed to 250°-260° and then rapidly heated up to 300°. The melt is cooled to room temperature, the oil is taken up in an alkaline aqueous solution, the pH of which is adjusted to 10, and the water/oil emulsion is extracted by shaking with chloroform. The chloroform solution is separated from the aqueous phase, dried with sodium sulphate and concentrated. The pink-beige needle crystals thus obtained melt at 69°-70° C.

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

Procedure: To a solution of 4-hydroxyphenylpropanenitrile (5.25 g) in N,N-dimethyl formamide (40 mL), 3-phenylpropyl bromide (7.1 g) and potassium carbonate (14.79 g) were added, followed by stirring at room temperature for 16 hours. Then, the reaction mixture was diluted with diethyl ether and an organic layer was successively washed with water and brine. After the organic layer was dried, the solvent was concentrated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give the title compound (8.54 g) having the following physical properties. an organic layer was successively washed with water and brine After the organic layer was dried the solvent was concentrated the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

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

Procedure: Finely ground 2-(4-aminophenyl) propionitrile (73 g., 0.5 mole) was suspended in concentrated hydrochloric acid (125 ml.). The stirred suspension was diazotised at 0°-5°C by the dropwise addition of a solution of sodium nitrite (36.23 g., 0.525 mole) in water (60 ml.) during 1-2 hours. The almost clear solution was stirred for a further 20 minutes at 5°-10°C, then poured into a stirred, boiling solution of concentrated sulphuric acid (250 ml.) in water (2.5 l.). After 6 minutes it was cooled in an ice-bath, then extracted with ether (x4). The combined ether extracts were extracted with 2N-sodium hydroxide solution (x6). The combined alkaline extracts were cooled in ice-bath, acidified with concentrated hydrochloric acid and extracted with ether (x3). The combined ether extracts were washed with saturated sodium chloride solution (x3), dried (Na2SO4) and evaporated to leave a dark brown oil (66.7 g.) which on distillation gave 2-(4-hydroxyphenyl) propionitrile (59.58 g.), b.p. 112°-122°C/0.125 m.m., m.p. 41°-46°C. poured into a stirred After 6 minutes it was cooled in an ice-bath extracted with ether (x4) The combined ether extracts were extracted with 2N-sodium hydroxide solution (x6) The combined alkaline extracts were cooled in ice-bath extracted with ether (x3) The combined ether extracts were washed with saturated sodium chloride solution (x3) dried (Na2SO4) evaporated to leave a dark brown oil (66.7 g.) which on distillation