decane-1-thiol

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

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

Procedure: A reaction was conducted as described in Example 1 except that tris[tris(dimethylamino)phosphoranylidene-amino]phosphine oxide was replaced with the same molar amount of a partially hydrated tris[tris(dimethylamino)phosphoranylidene-amino]phosphine oxide, [(Me2N)3P=N]3P=O.0.29H2O, phenol was replaced with the same molar amount of decanethiol and PGE was replaced with 2,3-epoxynorbornane. Desired 2-decylthio-3-hydroxynorbornane was formed in an analytical yield of 95% and isolated in a yield of 90%.

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 250 mL round-bottomed flask fitted with an overhead mechanical stirrer, a thermometer and an addition funnel were charged 87 g of 1-decanethiol and 20 drops of a 21% by weight solution of sodium ethoxide in ethanol. The mixture was cooled to 10° C. using an ice bath. Then the dropwise addition of 53 g of acrylonitrile was started. After addition of a portion of the acrylonitrile, 10 drops of 21% by weight solution of sodium ethoxide in ethanol were added. The temperature of the reaction mixture during the addition of the remaining acrylonitrile ranged between 30° C. and 35° C. The reaction mixture was then kept at room temperature overnight (~19 hours). The unreacted acrylonitrile was then removed by distillation at atmospheric pressure. The remaining material was then distilled at ~1 mm pressure. A first fraction was collected from 150° C. to 160° C. Fraction one had a strong odor of thiol. A second and final fraction was collected at 160° C. The second fraction had a faint odor of thiol. An NMR spectrum indicated the second fraction to be the desired product 83.5% of theoretical (94.9 g) based upon the weight of 1-decanethiol employed. To a 250 mL round-bottomed flask fitted with an overhead mechanical stirrer were added ranged between 30° C. and 35° C (~19 hours) The unreacted acrylonitrile was then removed by distillation at atmospheric pressure The remaining material was then distilled at ~1 mm pressure A first fraction was collected from 150° C. to 160° C A second and final fraction was collected at 160° C

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately 225 pounds of decylmercaptan are loaded into a jacketed reactor equipped with an agitator. 1.25 pounds of zinc chloride catalyst are added through the manhole. The system is heated to approximately 140° C. and 130 pounds of 2-ethyl-2-oxazoline are added at the rate of 3 lbs/min in about 45 minutes. About 30 minutes are allowed for the reaction to be completed, the reactor cooled to approximately 120° C. and 155 pounds of 32 weight percent hydrochloric acid are then added to the reaction mixture. The reactor is heated to 150°-160° C., at which time the vapor pressure of the system is approximately 60 psi. The temperature is maintained near 150° C. for 2 hours to complete the hydrolysis. equipped with an agitator About 30 minutes are allowed for the reaction the reactor cooled to approximately 120° C. The reactor is heated to 150°-160° C., at which time the vapor pressure of the system The temperature is maintained near 150° C. for 2 hours the hydrolysis

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

Procedure: The same operation as in Example 1-1 or 1-2 was carried out using trans-2-decenoic acid and 1-decanethiol as starting materials to give the aimed compound.

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 250 mL round-bottomed flask fitted with an overhead mechanical stirrer, a thermometer and an addition funnel were charged 87 g of 1-decanethiol and 20 drops of a 21% by weight solution of sodium ethoxide in ethanol. The mixture was cooled to 10° C. using an ice bath. Then the dropwise addition of 53 g of acrylonitrile was started. After addition of a portion of the acrylonitrile, 10 drops of 21% by weight solution of sodium ethoxide in ethanol were added. The temperature of the reaction mixture during the addition of the remaining acrylonitrile ranged between 30° C. and 35° C. The reaction mixture was then kept at room temperature overnight (~19 hours). The unreacted acrylonitrile was then removed by distillation at atmospheric pressure. The remaining material was then distilled at ~1 mm pressure. A first fraction was collected from 150° C. to 160° C. Fraction one had a strong odor of thiol. A second and final fraction was collected at 160° C. The second fraction had a faint odor of thiol. An NMR spectrum indicated the second fraction to be the desired product 83.5% of theoretical (94.9 g) based upon the weight of 1-decanethiol employed. To a 250 mL round-bottomed flask fitted with an overhead mechanical stirrer were added ranged between 30° C. and 35° C (~19 hours) The unreacted acrylonitrile was then removed by distillation at atmospheric pressure The remaining material was then distilled at ~1 mm pressure A first fraction was collected from 150° C. to 160° C A second and final fraction was collected at 160° C

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 250 mL round-bottomed flask fitted with an overhead mechanical stirrer, a thermometer and an addition funnel were charged 87 g of 1-decanethiol and 20 drops of a 21% by weight solution of sodium ethoxide in ethanol. The mixture was cooled to 10° C. using an ice bath. Then the dropwise addition of 53 g of acrylonitrile was started. After addition of a portion of the acrylonitrile, 10 drops of 21% by weight solution of sodium ethoxide in ethanol were added. The temperature of the reaction mixture during the addition of the remaining acrylonitrile ranged between 30° C. and 35° C. The reaction mixture was then kept at room temperature overnight (~19 hours). The unreacted acrylonitrile was then removed by distillation at atmospheric pressure. The remaining material was then distilled at ~1 mm pressure. A first fraction was collected from 150° C. to 160° C. Fraction one had a strong odor of thiol. A second and final fraction was collected at 160° C. The second fraction had a faint odor of thiol. An NMR spectrum indicated the second fraction to be the desired product 83.5% of theoretical (94.9 g) based upon the weight of 1-decanethiol employed. To a 250 mL round-bottomed flask fitted with an overhead mechanical stirrer were added ranged between 30° C. and 35° C (~19 hours) The unreacted acrylonitrile was then removed by distillation at atmospheric pressure The remaining material was then distilled at ~1 mm pressure A first fraction was collected from 150° C. to 160° C A second and final fraction was collected at 160° C

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

Procedure: In a 3000 ml flask equipped with a stirrer and a condenser were charged 132 g of 11-bromoundecanoic acid, 91.5 g of n-decanthiol, 59.4 g of sodium methoxide (28% methanol solution) and 1500 ml of methanol, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, precipitated crystals were collected by filtration under reduced pressure and the resulting crystals were washed with methanol. The resulting crystals were suspended in 5000 ml of distilled water, and the suspension was neutralized by a conc. hydrochloric acid, and the crystals were again collected by filtration under reduced pressure. The crystals were washed with water until the washed solution became neutral, and recrystallized from ethanol to obtain 140.5 g of the title compound. In a 3000 ml flask equipped with a stirrer and a condenser the mixture was refluxed for 12 hours After completion of the reaction precipitated crystals were collected by filtration under reduced pressure the resulting crystals were washed with methanol the crystals were again collected by filtration under reduced pressure The crystals were washed with water until the washed solution recrystallized from ethanol

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

Procedure: In a 3000 ml flask equipped with a stirrer and a condenser were charged 132 g of 11-bromoundecanoic acid, 91.5 g of n-decanthiol, 59.4 g of sodium methoxide (28% methanol solution) and 1500 ml of methanol, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, precipitated crystals were collected by filtration under reduced pressure and the resulting crystals were washed with methanol. The resulting crystals were suspended in 5000 ml of distilled water, and the suspension was neutralized by a conc. hydrochloric acid, and the crystals were again collected by filtration under reduced pressure. The crystals were washed with water until the washed solution became neutral, and recrystallized from ethanol to obtain 140.5 g of the title compound. In a 3000 ml flask equipped with a stirrer and a condenser the mixture was refluxed for 12 hours After completion of the reaction precipitated crystals were collected by filtration under reduced pressure the resulting crystals were washed with methanol the crystals were again collected by filtration under reduced pressure The crystals were washed with water until the washed solution recrystallized from ethanol

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

Procedure: 2 g (3.95 millimols) of 4,5-bis-(p-tolylthio)-3,6-dichlorophthalic acid N-2-hydroxyethylimide, 1,51 g (8.69 millimols) of n-decane-1-thiol, 2.29 g (16.58 millimols) of potassium carbonate and 20 ml of N,N-dimethylformamide are stirred at 25° C. for 1 hour. After concentration, the residue is taken up in methylene chloride/dilute HCl solution. The extracts are dried over sodium sulfate and evaporated. After precipitation from n-hexane, 300 mg (10% of theory) of the title compound (waxy substance) are obtained. After concentration The extracts are dried over sodium sulfate evaporated After precipitation from n-hexane, 300 mg (10% of theory) of the title compound (waxy substance) are obtained

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

Procedure: 2 g (6.08 millimols) of tetrachlorophthalic acid N-2-hydroxyethylimide, 5.30 g (30.4 millimols) of n-decanethiol, 6.30 g (45.6 millimols) of potassium carbonate and 20 ml of N,N-dimethylformamide are stirred at 25° C. for 7 hours. The mixture is acidified and extracted with methylene chloride. After recrystallisation from n-hexane at 0° C., 3.75 g (70% of theory) of the title compound are obtained; melting point 57°-8° C. extracted with methylene chloride After recrystallisation from n-hexane at 0° C.

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately 225 pounds of decylmercaptan are loaded into a jacketed reactor equipped with an agitator. 1.25 pounds of zinc chloride catalyst are added through the manhole. The system is heated to approximately 140° C. and 130 pounds of 2-ethyl-2-oxazoline are added at the rate of 3 lbs/min in about 45 minutes. About 30 minutes are allowed for the reaction to be completed, the reactor cooled to approximately 120° C. and 155 pounds of 32 weight percent hydrochloric acid are then added to the reaction mixture. The reactor is heated to 150°-160° C., at which time the vapor pressure of the system is approximately 60 psi. The temperature is maintained near 150° C. for 2 hours to complete the hydrolysis. equipped with an agitator About 30 minutes are allowed for the reaction the reactor cooled to approximately 120° C. The reactor is heated to 150°-160° C., at which time the vapor pressure of the system The temperature is maintained near 150° C. for 2 hours the hydrolysis