2-(phenyliminomethyl)phenol

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

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

Procedure: Lithium isopropoxide (300 mL, 20.7 g, 66.03 mmol) was added slowly to a solution of N-salicylideneaniline (61.83 g, 66.03 mmol) in dried acetonitrile (200 mL) under nitrogen atmosphere. A pale yellow precipitate was formed and was left stirring overnight. It was filtered off, washed thoroughly with acetonitrile and dried in vacuum oven for 8 hours at 80° C. Giving 61.6 g of product (97% yield). Sublimation (260° C., 10−6 Torr.) yielded an analytical sample (25.1 g from 29.2 g). A pale yellow precipitate was formed was left It was filtered off washed thoroughly with acetonitrile dried in vacuum oven for 8 hours at 80° C

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

Procedure: To a mixture of salicylaldehyde (40 mL, 45.84 g, 375.37 mmol)) and aniline (22 mL, 31.72 g, 374.66 mmol), was added ethanol (90 mL), 8 drops of concentrated hydrochloric acid and water (10 mL). This reaction mixture was refluxed for one hour, allowed to cool to room temperature and left in the refrigerator over the weekend. A large quantity of orange solid was formed after 2 hours in the refrigerator. It was filtered off and washed with ethanol. Recrystallisation from ethanol afforded 31.53 g of product. This reaction mixture was refluxed for one hour left in the refrigerator over the weekend A large quantity of orange solid was formed after 2 hours in the refrigerator It was filtered off washed with ethanol Recrystallisation from ethanol

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

Procedure: o-Hydroxybenzaldehyde (0.20 mole) is treated with aniline with vigorous stirring in a 1 l. Erlenmeyer Flask. After 15 mins., 33 cc of 95% ethanol is added and the reaction mixture is stirred vigorously for an additional 5 min. The reaction mixture is left standing at room temperature for 10 min., then it is placed in an ice-bath for 0.5 hr. The crystals which form are collected, washed with 95% ethanol, and air dried. Recrystallization from 85% ethanol yields N-(o-hydroxybenzylidene)aniline. m.p. 47°-49° C. the reaction mixture is stirred vigorously for an additional 5 min The reaction mixture is left standing at room temperature for 10 min. it is placed in an ice-bath for 0.5 hr The crystals which form are collected washed with 95% ethanol, and air dried Recrystallization from 85% ethanol

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

Procedure: o-Hydroxybenzaldehyde (0.20 mole) is treated with aniline with vigorous stirring in a 1 l. Erlenmeyer Flask. After 15 mins., 33 cc of 95% ethanol is added and the reaction mixture is stirred vigorously for an additional 5 min. The reaction mixture is left standing at room temperature for 10 min., then it is placed in an ice-bath for 0.5 hr. The crystals which form are collected, washed with 95% ethanol, and air dried. Recrystallization from 85% ethanol yields N-(o-hydroxybenzylidene)aniline. m.p. 47°-49° C. the reaction mixture is stirred vigorously for an additional 5 min The reaction mixture is left standing at room temperature for 10 min. it is placed in an ice-bath for 0.5 hr The crystals which form are collected washed with 95% ethanol, and air dried Recrystallization from 85% ethanol

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

Procedure: Lithium isopropoxide (300 mL, 20.7 g, 66.03 mmol) was added slowly to a solution of N-salicylideneaniline (61.83 g, 66.03 mmol) in dried acetonitrile (200 mL) under nitrogen atmosphere. A pale yellow precipitate was formed and was left stirring overnight. It was filtered off, washed thoroughly with acetonitrile and dried in vacuum oven for 8 hours at 80° C. Giving 61.6 g of product (97% yield). Sublimation (260° C., 10−6 Torr.) yielded an analytical sample (25.1 g from 29.2 g). A pale yellow precipitate was formed was left It was filtered off washed thoroughly with acetonitrile dried in vacuum oven for 8 hours at 80° C

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

Procedure: Lithium isopropoxide (300 mL, 20.7 g, 66.03 mmol) was added slowly to a solution of N-salicylideneaniline (61.83 g, 66.03 mmol) in dried acetonitrile (200 mL) under nitrogen atmosphere. A pale yellow precipitate was formed and was left stirring overnight. It was filtered off, washed thoroughly with acetonitrile and dried in vacuum oven for 8 hours at 80° C. Giving 61.6 g of product (97% yield). Sublimation (260° C., 10−6 Torr.) yielded an analytical sample (25.1 g from 29.2 g). A pale yellow precipitate was formed was left It was filtered off washed thoroughly with acetonitrile dried in vacuum oven for 8 hours at 80° C

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

Procedure: To a mixture of salicylaldehyde (40 mL, 45.84 g, 375.37 mmol)) and aniline (22 mL, 31.72 g, 374.66 mmol), was added ethanol (90 mL), 8 drops of concentrated hydrochloric acid and water (10 mL). This reaction mixture was refluxed for one hour, allowed to cool to room temperature and left in the refrigerator over the weekend. A large quantity of orange solid was formed after 2 hours in the refrigerator. It was filtered off and washed with ethanol. Recrystallisation from ethanol afforded 31.53 g of product. This reaction mixture was refluxed for one hour left in the refrigerator over the weekend A large quantity of orange solid was formed after 2 hours in the refrigerator It was filtered off washed with ethanol Recrystallisation from ethanol

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

Procedure: To a mixture of salicylaldehyde (40 mL, 45.84 g, 375.37 mmol)) and aniline (22 mL, 31.72 g, 374.66 mmol), was added ethanol (90 mL), 8 drops of concentrated hydrochloric acid and water (10 mL). This reaction mixture was refluxed for one hour, allowed to cool to room temperature and left in the refrigerator over the weekend. A large quantity of orange solid was formed after 2 hours in the refrigerator. It was filtered off and washed with ethanol. Recrystallisation from ethanol afforded 31.53 g of product. This reaction mixture was refluxed for one hour left in the refrigerator over the weekend A large quantity of orange solid was formed after 2 hours in the refrigerator It was filtered off washed with ethanol Recrystallisation from ethanol

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

Procedure: o-Hydroxybenzaldehyde (0.20 mole) is treated with aniline with vigorous stirring in a 1 l. Erlenmeyer Flask. After 15 mins., 33 cc of 95% ethanol is added and the reaction mixture is stirred vigorously for an additional 5 min. The reaction mixture is left standing at room temperature for 10 min., then it is placed in an ice-bath for 0.5 hr. The crystals which form are collected, washed with 95% ethanol, and air dried. Recrystallization from 85% ethanol yields N-(o-hydroxybenzylidene)aniline. m.p. 47°-49° C. the reaction mixture is stirred vigorously for an additional 5 min The reaction mixture is left standing at room temperature for 10 min. it is placed in an ice-bath for 0.5 hr The crystals which form are collected washed with 95% ethanol, and air dried Recrystallization from 85% ethanol

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

Procedure: o-Hydroxybenzaldehyde (0.20 mole) was treated with aniline with vigorous stirring in a 1 liter Erlenmeyer Flask. After 15 min., 33 cc of 95% ethanol was added and the reaction mixture was stirred vigorously for an additional 5 min. The reaction mixture was left standing at room temperature for 10 min., then it was placed in an ice-bath for 0.5 hour. The crystals which formed were collected, washed with 95% ethanol, and air dried. Recrystallization from 85% ethanol yielded N-(o-hydroxybenzylidene)aniline. m.p. 47°-49° C. the reaction mixture was stirred vigorously for an additional 5 min The reaction mixture was left standing at room temperature for 10 min. it was placed in an ice-bath for 0.5 hour The crystals which formed were collected washed with 95% ethanol, and air dried Recrystallization from 85% ethanol

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

Procedure: Lithium isopropoxide (300 mL, 20.7 g, 66.03 mmol) was added slowly to a solution of N-salicylideneaniline (61.83 g, 66.03 mmol) in dried acetonitrile (200 mL) under nitrogen atmosphere. A pale yellow precipitate was formed and was left stirring overnight. It was filtered off, washed thoroughly with acetonitrile and dried in vacuum oven for 8 hours at 80° C. Giving 61.6 g of product (97% yield). Sublimation (260° C., 10−6 Torr.) yielded an analytical sample (25.1 g from 29.2 g). A pale yellow precipitate was formed was left It was filtered off washed thoroughly with acetonitrile dried in vacuum oven for 8 hours at 80° C