4-(phenyliminomethyl)phenol

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

Procedure: A solution of hydroxy benzaldehyde (5.00 g, 41 mmol) in toluene (200 cm3) was heated to 109° C. before aniline (1.86 g, 20 mmol) was added under nitrogen. The mixture was then allowed to cool, forming a yellow solid after 30 minutes. The reaction was continued with the further addition of aniline (1.86 g, 20 mmol). Dean and Stark apparatus was used to collect water (0.6 cm3). Reflux continued for a further 5 hours by which time 0.7 cm3 of water had collected. After cooling the mixture, a thick crystalline mass was formed which was filtered and dried under vacuum at 90° C. to give 4-hydroxybenzylidene-aniline (7.3 g, 94%) as pale cream crystals. was added under nitrogen to cool forming a yellow solid after 30 minutes to collect water (0.6 cm3) Reflux had collected After cooling the mixture a thick crystalline mass was formed which was filtered dried under vacuum at 90° C.

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

Procedure: A solution of hydroxy benzaldehyde (5.00 g, 41 mmol) in toluene (200 cm3) was heated to 109° C. before aniline (1.86 g, 20 mmol) was added under nitrogen. The mixture was then allowed to cool, forming a yellow solid after 30 minutes. The reaction was continued with the further addition of aniline (1.86 g, 20 mmol). Dean and Stark apparatus was used to collect water (0.6 cm3). Reflux continued for a further 5 hours by which time 0.7 cm3 of water had collected. After cooling the mixture, a thick crystalline mass was formed which was filtered and dried under vacuum at 90° C. to give 4-hydroxybenzylidene-aniline (7.3 g, 94%) as pale cream crystals. was added under nitrogen to cool forming a yellow solid after 30 minutes to collect water (0.6 cm3) Reflux had collected After cooling the mixture a thick crystalline mass was formed which was filtered dried under vacuum at 90° C.

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

Procedure: A solution of hydroxy benzaldehyde (5.00 g, 41 mmol) in toluene (200 cm3) was heated to 109° C. before aniline (1.86 g, 20 mmol) was added under nitrogen. The mixture was then allowed to cool, forming a yellow solid after 30 minutes. The reaction was continued with the further addition of aniline (1.86 g, 20 mmol). Dean and Stark apparatus was used to collect water (0.6 cm3). Reflux continued for a further 5 hours by which time 0.7 cm3 of water had collected. After cooling the mixture, a thick crystalline mass was formed which was filtered and dried under vacuum at 90° C. to give 4-hydroxybenzylidene-aniline (7.3 g, 94%) as pale cream crystals. was added under nitrogen to cool forming a yellow solid after 30 minutes to collect water (0.6 cm3) Reflux had collected After cooling the mixture a thick crystalline mass was formed which was filtered dried under vacuum at 90° C.

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

Procedure: (a) To 170 ml of absolute ethanol is added 1.48 g of sodium, and 8.4 g of 4-(N-phenylformimidoyl)phenol is added to the mixture at room temperature with stirring to prepare a solution. 12.5 g of ethyl 2-bromo-2-methylpropionate is added to the solution, and the mixture is refluxed under heating for 5 hours. After the reaction, the ethanol is distilled off. The residue is dissolved in ether and thereafter washed with 5% aqueous solution of sodium hydroxide and then with water. After drying the resulting mixture, the ether is distilled off to give 9.2 g of ethyl 2-[4-(N-phenylformimidoyl)phenoxy]-2-methylpropionate. Infrared absorption spectrum (liquid film) 1735, 1280, 1245, 1170, 1140, 1020 cm-1. is added to the mixture at room temperature to prepare a solution the mixture is refluxed under heating for 5 hours After the reaction the ethanol is distilled off The residue is dissolved in ether washed with 5% aqueous solution of sodium hydroxide After drying the resulting mixture the ether is distilled off

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

Procedure: A solution of hydroxy benzaldehyde (5.00 g, 41 mmol) in toluene (200 cm3) was heated to 109° C. before aniline (1.86 g, 20 mmol) was added under nitrogen. The mixture was then allowed to cool, forming a yellow solid after 30 minutes. The reaction was continued with the further addition of aniline (1.86 g, 20 mmol). Dean and Stark apparatus was used to collect water (0.6 cm3). Reflux continued for a further 5 hours by which time 0.7 cm3 of water had collected. After cooling the mixture, a thick crystalline mass was formed which was filtered and dried under vacuum at 90° C. to give 4-hydroxybenzylidene-aniline (7.3 g, 94%) as pale cream crystals. was added under nitrogen to cool forming a yellow solid after 30 minutes to collect water (0.6 cm3) Reflux had collected After cooling the mixture a thick crystalline mass was formed which was filtered dried under vacuum at 90° C.