pentadecanoyl chloride

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

Procedure: Pentadecanoic acid (24.2g) was treated with thionyl chloride (13.1g) at 80°-90° C. Pentadecanoyl chloride, thus obtained, was added slowly under ice cooling into the mixture of β-phenoxyethylalcohol (13.8g), pyridine (10.3g) and benzene (100ml) with stirring. After having been stirred, the reaction mixture was treated with an ordinary method (washed with dilute hydrochloric acid, the benzene layer was dried over Glauber's salt, and then benzene was removed under reduced pressure, giving a crude product). Solid (33g) was obtained. The solid was recrystalized from n-hexane, from which it formed colourless crystals (26g), m.p. 45.0°-47.0° C., of β-phenoxyethyl pentadecanoate.

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

Procedure: Pentadecanoic acid (24.2g) was treated with thionyl chloride (13.1g) at 80°-90° C. Pentadecanoyl chloride, thus obtained, was added slowly under ice cooling into the mixture of β-phenoxyethylalcohol (13.8g), pyridine (10.3g) and benzene (100ml) with stirring. After having been stirred, the reaction mixture was treated with an ordinary method (washed with dilute hydrochloric acid, the benzene layer was dried over Glauber's salt, and then benzene was removed under reduced pressure, giving a crude product). Solid (33g) was obtained. The solid was recrystalized from n-hexane, from which it formed colourless crystals (26g), m.p. 45.0°-47.0° C., of β-phenoxyethyl pentadecanoate.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a one L three-necked flask were placed 31.9 g (0.24 mol) of L-aspartic acid and an aqueous solution of 19.2 g (0.48 mol) of sodium hydroxide in 150 mL of water under stirring. After the L-aspartic acid was dissolved, 120 mL of acetone was added to the mixture in the flask. Then, to the resultant reaction liquid which had been cooled to 0° C. were added dropwise over a period of 30 minutes, 52.2 g (0.2 mol) of pentadecanoyl chloride and an aqueous solution of 0.2N sodium hydroxide in 30 mL of water simultaneously therewith, while maintaining the reaction temperature at 0 to 5° C. and pH at 11 to 12. Thereafter, by gradually raising the temperature of the reaction liquid to room temperature (25° C) under stirring over a period of 2 hours, a solution of disodium pentadecanoyl-L-aspartate was obtained. To the resultant solution was added 140 mL of 5N hydrochloric acid to lower the pH of the solution to 1. The crystal thus precipitated was separated from the solution by means of vacuum filtration, washed with water and dried under reduced pressure. The resultant crystal was washed with 500 mL of hexane, dried and recrystallized from a mixed solvent of ethanol/water (1:1 v/v). As a result 39.8 g (0.11 mol) of N-pentadecanoyl-L-aspartic acid was obtained in a yield of 55.6% based on the fed pentadecanoyl chloride. The physical properties of the objective N-pentadecanoyl-L-aspartic acid were as follows. Then, to the resultant reaction liquid which were added dropwise over a period of 30 minutes Thereafter, by gradually raising the temperature of the reaction liquid to room temperature (25° C)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a one L three-necked flask were placed 31.9 g (0.24 mol) of L-aspartic acid and an aqueous solution of 19.2 g (0.48 mol) of sodium hydroxide in 150 mL of water under stirring. After the L-aspartic acid was dissolved, 120 mL of acetone was added to the mixture in the flask. Then, to the resultant reaction liquid which had been cooled to 0° C. were added dropwise over a period of 30 minutes, 52.2 g (0.2 mol) of pentadecanoyl chloride and an aqueous solution of 0.2N sodium hydroxide in 30 mL of water simultaneously therewith, while maintaining the reaction temperature at 0 to 5° C. and pH at 11 to 12. Thereafter, by gradually raising the temperature of the reaction liquid to room temperature (25° C) under stirring over a period of 2 hours, a solution of disodium pentadecanoyl-L-aspartate was obtained. To the resultant solution was added 140 mL of 5N hydrochloric acid to lower the pH of the solution to 1. The crystal thus precipitated was separated from the solution by means of vacuum filtration, washed with water and dried under reduced pressure. The resultant crystal was washed with 500 mL of hexane, dried and recrystallized from a mixed solvent of ethanol/water (1:1 v/v). As a result 39.8 g (0.11 mol) of N-pentadecanoyl-L-aspartic acid was obtained in a yield of 55.6% based on the fed pentadecanoyl chloride. The physical properties of the objective N-pentadecanoyl-L-aspartic acid were as follows. Then, to the resultant reaction liquid which were added dropwise over a period of 30 minutes Thereafter, by gradually raising the temperature of the reaction liquid to room temperature (25° C)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a one L (liter) two-necked flask were placed 160.0 g (0.66 mol) of pentadecanoic acid and 200 milliliter (mL) of cyclohexane, and the flask was equipped with a 100 mL dropping funnel containing 83.3 g (0.7 mol) of thionyl chloride and a reflux tube. Then, the pentadecanoic acid was completely dissolved under heating and stirring of the flask in an oil bath at 80° C. Thereafter the thionyl chloride was added dropwise over a period of 2 hours, and further the oil bath was maintained at 80° C. for one hour. From the resultant reaction mixture were removed the cyclohexane and the thionyl chloride under reduced pressure by means of an aspirator. The resultant crude reaction product was subjected to vacuum distillation. Thus 110.0 g (0.42 mol) of pentadecanoyl chloride was obtained in a yield of 63.9% based on the fed pentadecanoic acid. the flask was equipped with a 100 mL under heating further the oil bath was maintained at 80° C. for one hour From the resultant reaction mixture were removed the cyclohexane The resultant crude reaction product was subjected to vacuum distillation

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

Procedure: Pentadecanoic acid (24.2g) was treated with thionyl chloride (13.1g) at 80°-90° C. Pentadecanoyl chloride, thus obtained, was added slowly under ice cooling into the mixture of β-phenoxyethylalcohol (13.8g), pyridine (10.3g) and benzene (100ml) with stirring. After having been stirred, the reaction mixture was treated with an ordinary method (washed with dilute hydrochloric acid, the benzene layer was dried over Glauber's salt, and then benzene was removed under reduced pressure, giving a crude product). Solid (33g) was obtained. The solid was recrystalized from n-hexane, from which it formed colourless crystals (26g), m.p. 45.0°-47.0° C., of β-phenoxyethyl pentadecanoate.

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

Procedure: C 18 resin: Pentadecanoyl chloride was synthesized by reacting 10 ml of 2 M thionyl chloride in 10 ml of toluene with 1.5 gm pentadecanoic acid. After 40 minutes of refluxing, the remaining thionyl chloride and toluene were removed by distillation. 4 gm of the 3-amino-propyl resin was then incubated overnight with the freshly prepared pentadecanoyl chloride in pyridine. The next day, the resin was twice washed with methylene chloride and then three times more with methanol and dried. After 40 minutes of refluxing the remaining thionyl chloride and toluene were removed by distillation The next day, the resin was twice washed with methylene chloride three times more with methanol and dried

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a one L three-necked flask were placed 31.9 g (0.24 mol) of L-aspartic acid and an aqueous solution of 19.2 g (0.48 mol) of sodium hydroxide in 150 mL of water under stirring. After the L-aspartic acid was dissolved, 120 mL of acetone was added to the mixture in the flask. Then, to the resultant reaction liquid which had been cooled to 0° C. were added dropwise over a period of 30 minutes, 52.2 g (0.2 mol) of pentadecanoyl chloride and an aqueous solution of 0.2N sodium hydroxide in 30 mL of water simultaneously therewith, while maintaining the reaction temperature at 0 to 5° C. and pH at 11 to 12. Thereafter, by gradually raising the temperature of the reaction liquid to room temperature (25° C) under stirring over a period of 2 hours, a solution of disodium pentadecanoyl-L-aspartate was obtained. To the resultant solution was added 140 mL of 5N hydrochloric acid to lower the pH of the solution to 1. The crystal thus precipitated was separated from the solution by means of vacuum filtration, washed with water and dried under reduced pressure. The resultant crystal was washed with 500 mL of hexane, dried and recrystallized from a mixed solvent of ethanol/water (1:1 v/v). As a result 39.8 g (0.11 mol) of N-pentadecanoyl-L-aspartic acid was obtained in a yield of 55.6% based on the fed pentadecanoyl chloride. The physical properties of the objective N-pentadecanoyl-L-aspartic acid were as follows. Then, to the resultant reaction liquid which were added dropwise over a period of 30 minutes Thereafter, by gradually raising the temperature of the reaction liquid to room temperature (25° C)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a one L (liter) two-necked flask were placed 160.0 g (0.66 mol) of pentadecanoic acid and 200 milliliter (mL) of cyclohexane, and the flask was equipped with a 100 mL dropping funnel containing 83.3 g (0.7 mol) of thionyl chloride and a reflux tube. Then, the pentadecanoic acid was completely dissolved under heating and stirring of the flask in an oil bath at 80° C. Thereafter the thionyl chloride was added dropwise over a period of 2 hours, and further the oil bath was maintained at 80° C. for one hour. From the resultant reaction mixture were removed the cyclohexane and the thionyl chloride under reduced pressure by means of an aspirator. The resultant crude reaction product was subjected to vacuum distillation. Thus 110.0 g (0.42 mol) of pentadecanoyl chloride was obtained in a yield of 63.9% based on the fed pentadecanoic acid. the flask was equipped with a 100 mL under heating further the oil bath was maintained at 80° C. for one hour From the resultant reaction mixture were removed the cyclohexane The resultant crude reaction product was subjected to vacuum distillation

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

Procedure: Pentadecanoic acid (24.2g) was treated with thionyl chloride (13.1g) at 80°-90° C. Pentadecanoyl chloride, thus obtained, was added slowly under ice cooling into the mixture of β-phenoxyethylalcohol (13.8g), pyridine (10.3g) and benzene (100ml) with stirring. After having been stirred, the reaction mixture was treated with an ordinary method (washed with dilute hydrochloric acid, the benzene layer was dried over Glauber's salt, and then benzene was removed under reduced pressure, giving a crude product). Solid (33g) was obtained. The solid was recrystalized from n-hexane, from which it formed colourless crystals (26g), m.p. 45.0°-47.0° C., of β-phenoxyethyl pentadecanoate.