4-十二烷基苯酚

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This benzoxazine was prepared from 4-dodecylphenol (26.2 g, 100 mmol), 3-aminopropyltriethoxysilane (22.1 g, 100 mmol), paraformaldehyde (6.3 g, 210 mmol), and toluene (150 mL). The method to prepare this compound was the same as that used to make the previous benzoxazines. The final product was a clear, faint yellow liquid. The yield was 92%. The method to prepare this compound

反应条件: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A 2 liter round-bottomed flask was charged with magnesium turnings (12.2 g, 0.50 mole), methanol (133 ml), toluene (60 ml), and magnesium methoxide solution (10 ml of an 8% w/w solution of magnesium methoxide in methanol). The reaction mixture was heated to 45° C. at which point the magnesium dissolution became vigorous. The temperature of the reaction mixture was maintained between 45° and 55° C. Para-dodecyl phenol (128.0 g, 0.50 mol) dissolved in toluene (125 ml) was added in one portion to the reaction mixture which was then maintained at 65° C. for one hour. Glacial acetic acid (30.1 g, 0.50 mol) was added over a 1 hour period, while maintaining the reaction mixture at reflux (65°-66° C.). The reaction flask was then rigged for fractional distillation and the methanol/toluene azeotrope was distilled off until an internal temperature of 85° C. was reached. A total of 117 g of distillate, assaying 65% methanol and 35% toluene, was collected. Toluene (130 g) was added to the reaction mixture in one portion. Paraformaldehyde (45.0 g) slurried in toluene (90 g) was then added over a 90 minute period. During the addition, the reaction mixture was maintained at a temperature of 85°-90° C. allowing a continuous distillation of the volatile reaction by-products. When the paraformaldehyde addition was complete, the reaction mixture was maintained at 90° C. for an additional 90 minutes. The reaction mass was then cooled to 35° C. and 500 ml of 20% v/v sulfuric acid was added. The hydrolysis mass was then stirred for an additional 45 minutes. After phase separation, the organic phase was washed twice with 200 ml portions of water. The washed organic phase was then separated, dried and rendered free of the solvent to yield crude 5-dodecyl salicylaldehyde. A 65% yield was obtained. The temperature of the reaction mixture was maintained between 45° and 55° C was added in one portion to the reaction mixture which was then maintained at 65° C. for one hour while maintaining the reaction mixture at reflux (65°-66° C.) The reaction flask was then rigged for fractional distillation the methanol/toluene azeotrope was distilled off until an internal temperature of 85° C. was collected Toluene (130 g) was added to the reaction mixture in one portion was then added over a 90 minute period During the addition the reaction mixture was maintained at a temperature of 85°-90° C. a continuous distillation of the volatile reaction by-products When the paraformaldehyde addition the reaction mixture was maintained at 90° C. for an additional 90 minutes The reaction mass was then cooled to 35° C. 500 ml of 20% v/v sulfuric acid was added After phase separation the organic phase was washed twice with 200 ml portions of water The washed organic phase was then separated dried

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 7.5 g of the 4-dodecylphenol obtained in (1) above was dissolved in 25 ml of acetic acid and 12.6 ml of 30% aqueous nitric acid solution was dropwise added slowly to the resulting solution, and then the resulting mixture was subjected to reaction at about 10° C. for one hour. The reaction mixture was added to 35 g of ice water and the extraction with 35 ml of diethyl ether was conducted three times. The diethyl ether layer thus obtained was washed with 35 ml of 5% aqueous NaHCO3 solution, and then dried with MgSO4. Subsequently, the solvent was distilled off to obtain 5.93 g of 4-dodecyl-2-nitrophenol. the resulting mixture was subjected to reaction at about 10° C. for one hour the extraction with 35 ml of diethyl ether The diethyl ether layer thus obtained was washed with 35 ml of 5% aqueous NaHCO3 solution dried with MgSO4 Subsequently, the solvent was distilled off

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 7.5 g of the 4-dodecylphenol obtained in (1) above was dissolved in 25 ml of acetic acid and 12.6 ml of 30% aqueous nitric acid solution was dropwise added slowly to the resulting solution, and then the resulting mixture was subjected to reaction at about 10° C. for one hour. The reaction mixture was added to 35 g of ice water and the extraction with 35 ml of diethyl ether was conducted three times. The diethyl ether layer thus obtained was washed with 35 ml of 5% aqueous NaHCO3 solution, and then dried with MgSO4. Subsequently, the solvent was distilled off to obtain 5.93 g of 4-dodecyl-2-nitrophenol. the resulting mixture was subjected to reaction at about 10° C. for one hour the extraction with 35 ml of diethyl ether The diethyl ether layer thus obtained was washed with 35 ml of 5% aqueous NaHCO3 solution dried with MgSO4 Subsequently, the solvent was distilled off

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 16.75 g of dodecyl chloride was dropwise added to 7.0 g of phenol and the resulting mixture was subjected to reaction at 90° C. for 30 minutes. And then, 12.0 g of AlCl3 powder was added thereto mixture was further subjected to reaction at 100° C. for 4 hours. The reaction mixture was cooled and added to dilute hydrochloric acid. The resulting mixture was then subjected to extraction with two 50-ml portions of ethyl acetate. To the resulting solution of the reaction product in the ethyl acetate was added 80 ml of 3% aqueous sodium hydroxide solution, and the aqueous layer was then separated. To the aqueous layer was added conc hydrochloric acid to adjust the pH to 2, and the crystal, thus precipitated was filtered and washed with water to obtain 9.35 g of 4-hydroxyphenyl undecyl ketone. Subsequently, 8.0 g of the 4-hydroxyphenyl undecyl ketone thus obtained was mixed with 650 mg of a 5% active carbon-supported palladium and 100 ml of acetic acid, and the resulting mixture was subjected to reaction in a hydrogen gas stream at 50° C. for 15 hours to reduce the ketone. The reaction mixture was cooled and filtered, and acetic acid was distilled off to obtain 7.50 g of white, solid 4-dodecylphenol. was mixed with 650 mg of a 5% active carbon- The reaction mixture was cooled filtered acetic acid was distilled off

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 16.75 g of dodecyl chloride was dropwise added to 7.0 g of phenol and the resulting mixture was subjected to reaction at 90° C. for 30 minutes. And then, 12.0 g of AlCl3 powder was added thereto mixture was further subjected to reaction at 100° C. for 4 hours. The reaction mixture was cooled and added to dilute hydrochloric acid. The resulting mixture was then subjected to extraction with two 50-ml portions of ethyl acetate. To the resulting solution of the reaction product in the ethyl acetate was added 80 ml of 3% aqueous sodium hydroxide solution, and the aqueous layer was then separated. To the aqueous layer was added conc hydrochloric acid to adjust the pH to 2, and the crystal, thus precipitated was filtered and washed with water to obtain 9.35 g of 4-hydroxyphenyl undecyl ketone. Subsequently, 8.0 g of the 4-hydroxyphenyl undecyl ketone thus obtained was mixed with 650 mg of a 5% active carbon-supported palladium and 100 ml of acetic acid, and the resulting mixture was subjected to reaction in a hydrogen gas stream at 50° C. for 15 hours to reduce the ketone. The reaction mixture was cooled and filtered, and acetic acid was distilled off to obtain 7.50 g of white, solid 4-dodecylphenol. was mixed with 650 mg of a 5% active carbon- The reaction mixture was cooled filtered acetic acid was distilled off

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 7.5 g of the 4-dodecylphenol obtained in (1) above was dissolved in 25 ml of acetic acid and 12.6 ml of 30% aqueous nitric acid solution was dropwise added slowly to the resulting solution, and then the resulting mixture was subjected to reaction at about 10° C. for one hour. The reaction mixture was added to 35 g of ice water and the extraction with 35 ml of diethyl ether was conducted three times. The diethyl ether layer thus obtained was washed with 35 ml of 5% aqueous NaHCO solution, and then dried with MgSO4. Subsequently, the solvent was distilled off to obtain 5.93 g of 4-dodecyl-2-nitrophenol. the resulting mixture was subjected to reaction at about 10° C. for one hour the extraction with 35 ml of diethyl ether The diethyl ether layer thus obtained was washed with 35 ml of 5% aqueous NaHCO solution dried with MgSO4 Subsequently, the solvent was distilled off

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 16.75 g of dodecyl chloride was dropwise added to 7.0 g of phenol and the resulting mixture was subjected to reaction at 90° C. for 30 minutes. And then, 12.0 g of AlCl3 powder was added thereto and the resulting mixture was further subjected to reaction at 100° C. for 4 hours. The reaction mixture was cooled and added to dilute hydrochloric acid. The resulting mixture was then subjected to extraction with two 50-ml portions of ethyl acetate. To the resulting solution of the reaction product in the ethyl acetate was added 80 ml of 3% aqueous sodium hydroxide solution, and the aqueous layer was then separated. To the aqueous layer was added conc hydrochloric acid to adjust the pH to 2, and the crystal, thus precipitated was filtered and washed with water to obtain 9.35 g of 4-hydroxyphenyl undecyl ketone. Subsequently, 8.0 g of the 4-hydroxyphenyl undecyl ketone thus obtained was mixed with 650 mg of a 5% active carbon-supported palladium and 100 ml of acetic acid, and the resulting mixture was subjected to reaction in a hydrogen gas stream at 50° C. for 15 hours to reduce the ketone. The reaction mixture was cooled and filtered, and acetic acid was distilled off to obtain 7.50 g of white, solid 4-dodecylphenol. was mixed with 650 mg of a 5% active carbon- The reaction mixture was cooled filtered acetic acid was distilled off

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 16.75 g of dodecyl chloride was dropwise added to 7.0 g of phenol and the resulting mixture was subjected to reaction at 90° C. for 30 minutes. And then, 12.0 g of AlCl3 powder was added thereto and the resulting mixture was further subjected to reaction at 100° C. for 4 hours. The reaction mixture was cooled and added to dilute hydrochloric acid. The resulting mixture was then subjected to extraction with two 50-ml portions of ethyl acetate. To the resulting solution of the reaction product in the ethyl acetate was added 80 ml of 3% aqueous sodium hydroxide solution, and the aqueous layer was then separated. To the aqueous layer was added conc hydrochloric acid to adjust the pH to 2, and the crystal, thus precipitated was filtered and washed with water to obtain 9.35 g of 4-hydroxyphenyl undecyl ketone. Subsequently, 8.0 g of the 4-hydroxyphenyl undecyl ketone thus obtained was mixed with 650 mg of a 5% active carbon-supported palladium and 100 ml of acetic acid, and the resulting mixture was subjected to reaction in a hydrogen gas stream at 50° C. for 15 hours to reduce the ketone. The reaction mixture was cooled and filtered, and acetic acid was distilled off to obtain 7.50 g of white, solid 4-dodecylphenol. was mixed with 650 mg of a 5% active carbon- The reaction mixture was cooled filtered acetic acid was distilled off

反应条件: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A 2-liter round-bottomed flask was charged with magnesium turnings (12.2 g, 0.50 mole), methanol (133 ml), toluene (60 ml), and magnesium methoxide solution (10 ml of an 8% w/w solution of magnesium methoxide in methanol). The reaction mixture was heated to 45° C. at which point the magnesium dissolution became vigorous. The temperature of the reaction mixture was maintained between 45 and 55° C. Para-dodecyl phenol (128.0 g, 0.50 mol) dissolved in toluene (125 ml) was added in one portion to the reaction mixture which was then maintained at 65° C. for one hour. Glacial acetic acid (30.1 g, 0.50 mol) was added over a 1 hour period, while maintaining the reaction mixture at reflux (65-66° C.). The reaction flask was then rigged for fractional distillation and the methanol/toluene azeotrope was distilled off until an internal temperature of 85° C. was reached. A total of 117 g of distillate, assaying 65% methanol and 35% toluene, was collected. Toluene (130 g) was added to the reaction mixture in one portion. Paraformaldehyde (45.0 g) slurried in toluene (90 g) was then added over a 90 minute period. During the addition, the reaction mixture was maintained at a temperature of 85-90° C. allowing a continuous distillation of the volatile reaction by-products. When the paraformaldehyde addition was complete, the reaction mixture was maintained at 90° C. for an additional 90 minutes. The reaction mass as then cooled to 35° C. and 500 ml of 20% v/v sulfuric acid was added. The hydrolysis mass was then stirred for an additional 45 minutes. After phase separation, the organic phase was washed twice with 200 ml portions of water. The washed organic phase was then separated, dried and rendered free of the solvent to yield crude 5-dodecyl salicylaldehyde. A 65% yield was obtained. The temperature of the reaction mixture was maintained between 45 and 55° C was added in one portion to the reaction mixture which was then maintained at 65° C. for one hour while maintaining the reaction mixture at reflux (65-66° C.) The reaction flask was then rigged for fractional distillation the methanol/toluene azeotrope was distilled off until an internal temperature of 85° C. was collected Toluene (130 g) was added to the reaction mixture in one portion was then added over a 90 minute period During the addition the reaction mixture was maintained at a temperature of 85-90° C. a continuous distillation of the volatile reaction by-products When the paraformaldehyde addition the reaction mixture was maintained at 90° C. for an additional 90 minutes The reaction mass as then cooled to 35° C. 500 ml of 20% v/v sulfuric acid was added After phase separation the organic phase was washed twice with 200 ml portions of water The washed organic phase was then separated dried

反应条件: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A 2-liter round-bottomed flask was charged with magnesium turnings (12.2 g, 0.50 mole), methanol (133 ml), toluene (60 ml), and magnesium methoxide solution (10 ml of an 8% w/w solution of magnesium methoxide in methanol). The reaction mixture was heated to 45° C. at which point the magnesium dissolution became vigorous. The temperature of the reaction mixture was maintained between 45 and 55° C. Para-dodecyl phenol (128.0 g, 0.50 mol) dissolved in toluene (125 ml) was added in one portion to the reaction mixture which was then maintained at 65° C. for one hour. Glacial acetic acid (30.1 g, 0.50 mol) was added over a 1 hour period, while maintaining the reaction mixture at reflux (65-66° C.). The reaction flask was then rigged for fractional distillation and the methanol/toluene azeotrope was distilled off until an internal temperature of 85° C. was reached. A total of 117 g of distillate, assaying 65% methanol and 35% toluene, was collected. Toluene (130 g) was added to the reaction mixture in one portion. Paraformaldehyde (45.0 g) slurried in toluene (90 g) was then added over a 90 minute period. During the addition, the reaction mixture was maintained at a temperature of 85-90° C. allowing a continuous distillation of the volatile reaction by-products. When the paraformaldehyde addition was complete, the reaction mixture was maintained at 90° C. for an additional 90 minutes. The reaction mass as then cooled to 35° C. and 500 ml of 20% v/v sulfuric acid was added. The hydrolysis mass was then stirred for an additional 45 minutes. After phase separation, the organic phase was washed twice with 200 ml portions of water. The washed organic phase was then separated, dried and rendered free of the solvent to yield crude 5-dodecyl salicylaldehyde. A 65% yield was obtained. The temperature of the reaction mixture was maintained between 45 and 55° C was added in one portion to the reaction mixture which was then maintained at 65° C. for one hour while maintaining the reaction mixture at reflux (65-66° C.) The reaction flask was then rigged for fractional distillation the methanol/toluene azeotrope was distilled off until an internal temperature of 85° C. was collected Toluene (130 g) was added to the reaction mixture in one portion was then added over a 90 minute period During the addition the reaction mixture was maintained at a temperature of 85-90° C. a continuous distillation of the volatile reaction by-products When the paraformaldehyde addition the reaction mixture was maintained at 90° C. for an additional 90 minutes The reaction mass as then cooled to 35° C. 500 ml of 20% v/v sulfuric acid was added After phase separation the organic phase was washed twice with 200 ml portions of water The washed organic phase was then separated dried