2-phenoxybenzaldehyde

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

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

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 2-phenoxybenzaldehyde (535 mg) in tetrahydrofuran (5 ml), 0.326 ml of diiodomethane and 5.4 ml of methyllithium (1.0M diethyl ether solution) were added under ice-cooling, and the reaction solution was stirred at the same temperature for 30 minutes and then at room temperature for 1 hour. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil. To a solution of the crude product in tetrahydrofuran (5 ml), 284 mg of sodium cyanoborohydride and 0.569 ml of trifluoroborane-diethyl ether complex were added under ice-cooling, and the reaction solution was stirred at the same temperature for 50 minutes. To the reaction solution was added a saturated saline solution, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (95:5-50/50)) to afford the title compound as a colorless oil. cooling at room temperature for 1 hour the mixture was extracted with ethyl acetate The combined organic layers were washed with a saturated saline solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil cooling the reaction solution was stirred at the same temperature for 50 minutes To the reaction solution was added a saturated saline solution the mixture was extracted with ethyl acetate The combined organic layers were washed with a saturated saline solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (95:5-50/50))

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-fluorobenzaldehyde (0.5 ml) in dimethylformamide (5 ml), 676 mg of phenol and 993 mg of potassium carbonate were added, and the reaction solution was stirred overnight at 100° C. The reaction solution was cooled, then 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50/50)) to afford the title compound as a pale yellow oil. The reaction solution was cooled the mixture was extracted with ethyl acetate The combined organic layers were washed with a saturated saline solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50/50))

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2-phenoxybenzaldehyde (4.96 g, 0,025 mole) were added anhydrous methanol (50 ml) and hydroxylamine hydrochloride (2.08 g, 0.03 mole), and the mixture was stirred at 60° C. for 3 hours. After completion of the reaction, water (200 ml) was added to the reaction mixture, which was extracted with methylene chloride and dried over magnesium sulfate. The crude product obtained by concentration under reduced pressure was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain 2-phenoxybenzaldoxime (3.95 g, yield: 74.1%) as a colorless oil. was added to the reaction mixture, which was extracted with methylene chloride dried over magnesium sulfate The crude product obtained by concentration under reduced pressure was purified by silica gel chromatography (ethyl acetate/n-hexane)

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

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2-phenoxybenzaldehyde (4.96 g, 0.025 mole) were added anhydrous methanol (50 ml) and hydroxylamine hydrochloride (2.08 g, 0.03 mole), and the mixture was stirred at 60° C. for 3 hours. After completion of the reaction, water (200 ml) was added to the reaction mixture, which was extracted with methylene chloride and dried over magnesium sulfate. The crude product obtained by concentration under reduced pressure was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain 2-phenoxybenzaldoxime (3.95 g, yield: 74.1%) as a colorless oil. was added to the reaction mixture, which was extracted with methylene chloride dried over magnesium sulfate The crude product obtained by concentration under reduced pressure was purified by silica gel chromatography (ethyl acetate/n-hexane)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2-phenoxybenzaldehyde (4.96 g, 0.025 mole) were added anhydrous methanol (50 ml) and hydroxylamine hydrochloride (2.08 g, 0.03 mole), and the mixture was stirred at 60° C. for 3 hours. After completion of the reaction, water (200 ml) was added to the reaction mixture, which was extracted with methylene chloride and dried over magnesium sulfate. The crude product obtained by concentration under reduced pressure was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain 2-phenoxybenzaldoxime (3.95 g, yield: 74.1%) as a colorless oil. was added to the reaction mixture, which was extracted with methylene chloride dried over magnesium sulfate The crude product obtained by concentration under reduced pressure was purified by silica gel chromatography (ethyl acetate/n-hexane)

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

Procedure: A mixture of 2-phenoxybenzaldehyde (2.12 g; 10.70 mmol) and methyl (triphenylphos-phoranylidene)acetate (4.01 g; 11.76 mmol) in 60 mL of THF was refluxed overnight. The reaction was cooled, diluted with ethyl acetate (50 mL) and washed with water (3X). The crude residue Was purified on a silica gel column eluting with hexane to obtain 1.4 g (52%) of 2-phenoxycinnamic acid, 1H NMR (CDCl3): δ 3.78 (s, 3H); 6.56 (d, 1H, J=16.1); 6.87 (d, 1H, J=8.5); 7.00 (d, 2H, J=7.5); 7.10-7.15 (m,2H); 7.28-7.33 (m, 3H); 7.36 (d, 1H, J=8.5); 8.02 (d, 2H, J=16.2). was refluxed overnight The reaction was cooled washed with water (3X) The crude residue Was purified on a silica gel column eluting with hexane

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

Procedure: A mixture of 2-phenoxybenzaldehyde (2.12 g; 10.70 mmol) and methyl (triphenylphos-phoranylidene)acetate (4.01 g; 11.76 mmol) in 60 mL of THF was refluxed overnight. The reaction was cooled, diluted with ethyl acetate (50 mL) and washed with water (3X). The crude residue Was purified on a silica gel column eluting with hexane to obtain 1.4 g (52%) of 2-phenoxycinnamic acid, 1H NMR (CDCl3): δ 3.78 (s, 3H); 6.56 (d, 1H, J=16.1); 6.87 (d, 1H, J=8.5); 7.00 (d, 2H, J=7.5); 7.10-7.15 (m,2H); 7.28-7.33 (m, 3H); 7.36 (d, 1H, J=8.5); 8.02 (d, 2H, J=16.2). was refluxed overnight The reaction was cooled washed with water (3X) The crude residue Was purified on a silica gel column eluting with hexane