2-hydroxy-4-octoxybenzaldehyde

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2-hydroxy-4-octyloxy-benzaldehyde (3.64 g; 14.5 mmol) in abs. EtOH (30 mL) was added hydroxylamine hydrochloride [50% H2O (w/w)] and the slurry was stirred for 2 hours. The reaction mixture was evaporated to dryness and the resulting solid triturated in H2O (20 mL) and EtOAc/diethylether (20 mL+10 mL) to give 1.8 g (47%) as a white solid. MS (direct; EI): 265 (M). The reaction mixture was evaporated to dryness the resulting solid triturated in H2O (20 mL) EtOAc/diethylether (20 mL+10 mL) to give 1.8 g (47%) as a white solid

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2-hydroxy-4-octyloxy-benzaldehyde (3.64 g; 14.5 mmol) in abs. EtOH (30 mL) was added hydroxylamine hydrochloride [50% H2O (w/w)] and the slurry was stirred for 2 hours. The reaction mixture was evaporated to dryness and the resulting solid triturated in H2O (20 mL) and EtOAc/diethylether (20 mL+10 mL) to give 1.8 g (47%) as a white solid. MS (direct; EI): 265 (M). The reaction mixture was evaporated to dryness the resulting solid triturated in H2O (20 mL) EtOAc/diethylether (20 mL+10 mL) to give 1.8 g (47%) as a white solid

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture of dimethylmalonate (4 ml), 2-hydroxy-4-octyloxybenzaldehyde (2.50 g) and piperidine (0.1 ml) in methanol (10 ml) was added acetic acid (0.01 ml), and the mixture was stirred for 3 hours at 70° C. The solvents were removed under reduced pressure, and the residue was dissolved in ethyl acetate, and washed with 0.5N hydrochloric acid, water and brine, and dried over magnesium sulfate. The magnesium sulfate was filtered off, and filtrate was evaporated under reduced pressure, and the precipitate was collected by filtration, and washed with n-hexane, and dried to give Methyl 7-octyloxycoumarin-3-carboxylate (0.94 g). The solvents were removed under reduced pressure the residue was dissolved in ethyl acetate washed with 0.5N hydrochloric acid, water and brine dried over magnesium sulfate The magnesium sulfate was filtered off filtrate was evaporated under reduced pressure the precipitate was collected by filtration washed with n-hexane dried

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2,4-Dihydroxybenzaldehyde (5.52 g), potassium carbonate (6.08 g) and octyl bromide (7.73 g) in acetonitrile (55 ml) was stirred for 16 hours at 60° C. The solvent of reaction mixture was removed under reduced pressure, and the residue was dissolved in ethyl acetate, and washed with water and brine. The separated organic layer was dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with (hexane : ethyl acetate=9:1) to give 2-Hydroxy-4-octyloxybenzaldehyde (6.73 g). The solvent of reaction mixture was removed under reduced pressure the residue was dissolved in ethyl acetate washed with water and brine The separated organic layer was dried over magnesium sulfate The magnesium sulfate was filtered off the filtrate was evaporated under reduced pressure eluted with (hexane : ethyl acetate=9:1)

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture of dimethylmalonate (4ml), 2-hydroxy-4-octyloxybenzaldehyde (2.50 g) and piperidine (0.1 ml) in methanol (10 ml) was added acetic acid (0.01 ml), and the mixture was stirred for 3 hours at 70° C. The solvents were removed under reduced pressure, and the residue was dissolved in ethyl acetate, and washed with 0.5N hydrochloric acid, water and brine, and dried over magnesium sulfate. The magnesium sulfate was filtered off, and filtrate was evaporated under reduced pressure, and the precipitate was collected by filtration, and washed with n-hexane, and dried to give Methyl 7-octyloxycoumarin-3-carboxylate (0.94 g). The solvents were removed under reduced pressure the residue was dissolved in ethyl acetate washed with 0.5N hydrochloric acid, water and brine dried over magnesium sulfate The magnesium sulfate was filtered off filtrate was evaporated under reduced pressure the precipitate was collected by filtration washed with n-hexane dried

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2,4-Dihydroxybenzaldehyde (5.52 g), potassium carbonate (6.08 g) and octyl bromide (7.73 g) in acetonitrile (55 ml) was stirred for 16 hours at 60° C. The solvent of reaction mixture was removed under reduced pressure, and the residue was dissolved in ethyl acetate, and washed with water and brine. The separated organic layer was dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with (hexane:ethyl acetate=9:1) to give 2-Hydroxy-4-octyloxybenzaldehyde (6.73 g). The solvent of reaction mixture was removed under reduced pressure the residue was dissolved in ethyl acetate washed with water and brine The separated organic layer was dried over magnesium sulfate The magnesium sulfate was filtered off the filtrate was evaporated under reduced pressure eluted with (hexane:ethyl acetate=9:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2-hydroxy-4-octyloxy-benzaldehyde (3.64 g; 14.5 mmol) in abs. EtOH (30 mL) was added hydroxylamine hydrochloride [50% H2O (w/w)] and the slurry was stirred for 2 hours. The reaction mixture was evaporated to dryness and the resulting solid triturated in H2O (20 mL) and EtOAc/diethylether (20 mL+10 mL) to give 1.8 g (47%) as a white solid. MS (direct; EI): 265 (M). The reaction mixture was evaporated to dryness the resulting solid triturated in H2O (20 mL) EtOAc/diethylether (20 mL+10 mL) to give 1.8 g (47%) as a white solid