4-dodecoxybenzaldehyde

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Hydroxybenzaldehyde (673 mg, 5.5 mmol), 1-bromododecane (1.25 g, 5 mmol) and potassium carbonate (859 mg, 6.22 mmol) were added to dimethylformamide (3 ml), and they were stirred at 65° C. for 18 hours. After the completion of the reaction followed by the extraction with ethyl acetate, 4-dodecyloxybenzaldehyde (yield: 1.45 g, 99%) was obtained in the form of white crystals. After the completion of the reaction followed by the extraction with ethyl acetate

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

実験手順: A solution of 4-(dodecyloxy)-benzaldehyde (10 g, 35 mmol) in THF (80 mL) was added dropwise to a stirred suspension of NaBH4 (2.7 g, 70 mmol) in dry THF (70 mL) at 0° C. The reaction mixture was stirred at room temperature overnight and was quenched with a small amount of water (5 mL). The solid formed was removed by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in CHCl3 (50 mL). The resulting solution was washed with brine (3×20 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to give a white powder (9.56 g, 94%). 1H NMR (400 MHz, CDCl3, δ): 7.29 (d, J=8.4 Hz, 2H), 6.90 (d, J=8.8 Hz, 2H), 4.62 (d, J=6.0 Hz, 2H), 3.97 (t, J=6.8 Hz, 2H), 1.79-1.51 (m, 2H), 1.51-1.26 (m, 19H), 0.90 (t, J=6.4 Hz, 3H). was quenched with a small amount of water (5 mL) The solid formed was removed by filtration the filtrate was concentrated in vacuo The residue was dissolved in CHCl3 (50 mL) The resulting solution was washed with brine (3×20 mL) dried over anhydrous Na2SO4 concentrated in vacuo

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

実験手順: Potassium carbonate (24.8 g, 180 mmol) was added to a solution of 4-hydroxybenzaldehyde (3.66 g, 30 mmol) in DMF (90 mL) at room temperature. After the mixture was stirred at 60° C. for 1 h, 1-bromooctane (8.7 mL, 36 mmol) was added slowly. The reaction mixture was stirred overnight at 80° C. under N2, cooled to room temperature, and poured over 200 mL of icy water. The mixture was extracted with EtOAc (3×50 mL). The combined organic phase was washed with brine (100 mL), dried over MgSO4, and concentrated in vacuo to give a yellow oil (13.67 g). 1H NMR (400 MHz, CDCl3, δ): 9.88 (s, 1H), 7.84 (d, J=8.7 Hz, 2H), 7.00 (d, J=8.7 Hz, 2H), 4.06 (t, J=6.6 Hz, 2H), 1.83-1.76 (m, 2H), 1.62-1.23 (m, 18H), 0.90 (t, J=8.8 Hz, 3H). The reaction mixture was stirred overnight at 80° C. under N2 cooled to room temperature The mixture was extracted with EtOAc (3×50 mL) The combined organic phase was washed with brine (100 mL) dried over MgSO4 concentrated in vacuo

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

実験手順: Potassium carbonate (24.8 g, 180 mmol) was added to a solution of 4-hydroxybenzaldehyde (3.66 g, 30 mmol) in DMF (90 mL) at room temperature. After the mixture was stirred at 60° C. for 1 h, 1-bromooctane (8.7 mL, 36 mmol) was added slowly. The reaction mixture was stirred overnight at 80° C. under N2, cooled to room temperature, and poured over 200 mL of icy water. The mixture was extracted with EtOAc (3×50 mL). The combined organic phase was washed with brine (100 mL), dried over MgSO4, and concentrated in vacuo to give a yellow oil (13.67 g). 1H NMR (400 MHz, CDCl3, δ): 9.88 (s, 1H), 7.84 (d, J=8.7 Hz, 2H), 7.00 (d, J=8.7 Hz, 2H), 4.06 (t, J=6.6 Hz, 2H), 1.83-1.76 (m, 2H), 1.62-1.23 (m, 18H), 0.90 (t, J=8.8 Hz, 3H). The reaction mixture was stirred overnight at 80° C. under N2 cooled to room temperature The mixture was extracted with EtOAc (3×50 mL) The combined organic phase was washed with brine (100 mL) dried over MgSO4 concentrated in vacuo

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

実験手順: 100 g of 4-hydroxy-benzaldehyde are reacted with 224.5 g of dodecyloxybromide along with 56.7 g of anhydrous KOH (85%) in 11 of 4-methyl-2-hydroxy-pentane. The mixture is then heated to reflux and maintained at reflux for 7 hours. The cooled reaction mixture is filtered to eliminate salts and distilled in a claisen equipment. 184 g (yield 77%) of a clear oil are collected at 178-181° C. and 0.5 mbar, which slowly crystallises on standing at room temperature. The mixture is then heated to reflux maintained at reflux for 7 hours The cooled reaction mixture is filtered distilled in a claisen equipment

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

実験手順: 100 g of 4-hydroxy-benzaldehyde are reacted with 224.5 g of dodecyloxybromide along with 56.7 g of anhydrous KOH (85%) in 11 of 4-methyl-2-hydroxy-pentane. The mixture is then heated to reflux and maintained at reflux for 7 hours. The cooled reaction mixture is filtered to eliminate salts and distilled in a claisen equipment. 184 g (yield 77%) of a clear oil are collected at 178-181° C. and 0.5 mbar, which slowly crystallises on standing at room temperature. The mixture is then heated to reflux maintained at reflux for 7 hours The cooled reaction mixture is filtered distilled in a claisen equipment

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

実験手順: 100 g of 4-hydroxy-benzaldehyde are reacted with 224.5 g of dodecyloxybromide along with 56.7 g of anhydrous KOH (85%) in 11 of 4-methyl-2-hydroxy-pentane. The mixture is then heated to reflux and maintained at reflux for 7 hours. The cooled reaction mixture is filtered to eliminate salts and distilled in a claisen equipment. 184 g (yield 77%) of a clear oil are collected at 178-181° C. and 0.5 mbar, which slowly crystallises on standing at room temperature. The mixture is then heated to reflux maintained at reflux for 7 hours The cooled reaction mixture is filtered distilled in a claisen equipment

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

実験手順: 4-Hydroxybenzaldehyde (5.0 g, 41 mmol, 1.0 equiv.), potassium carbonate (8.5 g, 61 mmol, 1.5 equiv.), dodecyl bromide (12.3 g, 49.2 mmol, 1.20 equiv.), and 18-crown-6 (1.0 g, 4.1 mmol, 0.10 equiv.) were placed in a flask with a magnetic stirring bar and a cooling column, and dissolved in 50 ml of acetone. The mixture was refluxed for 24 h. After cooling down, the mixture was filtered and concentrated in vacuo. The crude product was subjected to a column chromatography using CH2Cl2 to afford the product as pale yellow solid (10.3 g, 35.0 mmol, 87% yield). 1H NMR (400 MHz, CDCl3) δ: 9.85 (s, 1H), 7.83 (d, 2H, J=8.6 Hz), 7.00 (d, 2H, J=8.6 Hz), 4.05 (t, 2H, J=6.4 Hz), 1.80 (m, 2H), 1.27 (m, 18H), 0.89 (t, 3H, J=6.7 Hz); 13C NMR (500 MHz, CDCl3) δ: 191.0, 164.5, 132.2, 130.0, 115.0, 68.7, 32.2, 29.9, 29.8, 29.6, 29.3, 26.2, 22.9, 14.4; APCI-MS m/z 291.3 (M+). The mixture was refluxed for 24 h After cooling down the mixture was filtered concentrated in vacuo

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

実験手順: 4-Hydroxybenzaldehyde (5.0 g, 41 mmol, 1.0 equiv.), potassium carbonate (8.5 g, 61 mmol, 1.5 equiv.), dodecyl bromide (12.3 g, 49.2 mmol, 1.20 equiv.), and 18-crown-6 (1.0 g, 4.1 mmol, 0.10 equiv.) were placed in a flask with a magnetic stirring bar and a cooling column, and dissolved in 50 ml of acetone. The mixture was refluxed for 24 h. After cooling down, the mixture was filtered and concentrated in vacuo. The crude product was subjected to a column chromatography using CH2Cl2 to afford the product as pale yellow solid (10.3 g, 35.0 mmol, 87% yield). 1H NMR (400 MHz, CDCl3) δ: 9.85 (s, 1H), 7.83 (d, 2H, J=8.6 Hz), 7.00 (d, 2H, J=8.6 Hz), 4.05 (t, 2H, J=6.4 Hz), 1.80 (m, 2H), 1.27 (m, 18H), 0.89 (t, 3H, J=6.7 Hz); 13C NMR (500 MHz, CDCl3) δ: 191.0, 164.5, 132.2, 130.0, 115.0, 68.7, 32.2, 29.9, 29.8, 29.6, 29.3, 26.2, 22.9, 14.4; APCI-MS m/z 291.3 (M+). The mixture was refluxed for 24 h After cooling down the mixture was filtered concentrated in vacuo

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

実験手順: 4-Hydroxybenzaldehyde (5.0 g, 41 mmol, 1.0 equiv.), potassium carbonate (8.5 g, 61 mmol, 1.5 equiv.), dodecyl bromide (12.3 g, 49.2 mmol, 1.20 equiv.), and 18-crown-6 (1.0 g, 4.1 mmol, 0.10 equiv.) were placed in a flask with a magnetic stirring bar and a cooling column, and dissolved in 50 ml of acetone. The mixture was refluxed for 24 h. After cooling down, the mixture was filtered and concentrated in vacuo. The crude product was subjected to a column chromatography using CH2Cl2 to afford the product as pale yellow solid (10.3 g, 35.0 mmol, 87% yield). 1H NMR (400 MHz, CDCl3) δ: 9.85 (s, 1H), 7.83 (d, 2H, J=8.6 Hz), 7.00 (d, 2H, J=8.6 Hz), 4.05 (t, 2H, J=6.4 Hz), 1.80 (m, 2H), 1.27 (m, 18H), 0.89 (t, 3H, J=6.7 Hz); 13C NMR (500 MHz, CDCl3) δ: 191.0, 164.5, 132.2, 130.0, 115.0, 68.7, 32.2, 29.9, 29.8, 29.6, 29.3, 26.2, 22.9, 14.4; APCI-MS m/z 291.3 (M+). The mixture was refluxed for 24 h After cooling down the mixture was filtered concentrated in vacuo

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Hydroxybenzaldehyde (673 mg, 5.5 mmol), 1-bromododecane (1.25 g, 5 mmol) and potassium carbonate (859 mg, 6.22 mmol) were added to dimethylformamide (3 ml), and they were stirred at 65° C. for 18 hours. After the completion of the reaction followed by the extraction with ethyl acetate, 4-dodecyloxybenzaldehyde (yield: 1.45 g, 99%) was obtained in the form of white crystals. After the completion of the reaction followed by the extraction with ethyl acetate

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Hydroxybenzaldehyde (673 mg, 5.5 mmol), 1-bromododecane (1.25 g, 5 mmol) and potassium carbonate (859 mg, 6.22 mmol) were added to dimethylformamide (3 ml), and they were stirred at 65° C. for 18 hours. After the completion of the reaction followed by the extraction with ethyl acetate, 4-dodecyloxybenzaldehyde (yield: 1.45 g, 99%) was obtained in the form of white crystals. After the completion of the reaction followed by the extraction with ethyl acetate