tridecan-2-one

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: A reactor equipped with a stirrer, reflux-condenser, thermometer and nitrogen gas inlet pipe was charged with 297 g of 2-tridecanone, 166 g of glycerol and a solvent amount of toluene, and following addition of p-toluenesulfonic acid as a catalyst, the dehydrative condensation reaction was carried out at the reflux temperature for 24 hours. The resulting crude product was washed with an aqueous solution of potassium carbonate and further with 3 portions of distilled water and finally purified by distillation under reduced pressure to provide 2-methyl-2-undecyl-4-hydroxymethyl-1,3-dioxolane. A reactor equipped with a stirrer, reflux-condenser the dehydrative condensation reaction The resulting crude product was washed with an aqueous solution of potassium carbonate and further with 3 portions of distilled water finally purified by distillation under reduced pressure

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

Procedure: A solution of n-butyllithium (12.6 mL, 27.7 mmol, 2.2 M in hexane) was added dropwise via syringe to a cooled (-78° C.) solution of diisopropylamine (4.1 mL, 29 mmol) in dry THF (200 mL). The resulting solution was stirred (15 minutes -78° C.), then a solution of 2-tridecanone (5.0 g, 25 mmol) in dry THF (50 mL) was added dropwise via a drop-in funnel. The resulting mixture was stirred (30 minutes, -78° C.), then a solution of chlorotrimethylsilane (3.5 mL, 28 mmol) in dry THF (40 mL) was added in one portion. The dry ice bath was removed and the resulting mixture was warmed to 10° C., then quenched with saturated sodium bicarbonate (100 mL). Dichloromethane (400 mL) and water (80 mL) were added and the layers were separated. The organic layer was washed with brine (1×200 mL), dried (MgSO4), and concentrated in vacuo to yield 6.7 g (98%) of the title compound as a milky oil which was used without further purification. The resulting mixture was stirred (30 minutes, -78° C.) The dry ice bath was removed quenched with saturated sodium bicarbonate (100 mL) Dichloromethane (400 mL) and water (80 mL) were added the layers were separated The organic layer was washed with brine (1×200 mL) dried (MgSO4) concentrated in vacuo

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

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

Procedure: Prepared from glyoxylic acid (4.94 g, 6.5 mmol), 2-tridecanone (12.9 g, 6.5 mmol) and orthophosphoric acid (20 ml). 1H n.m.r. δ (CDCl3) 0.87, t J 7.2 Hz, 3H, CH3; 1.30, m, 16H, CH2; 2.39, s, 3H, CH3; 2.77, t J 7.0 Hz, 2H, CH2; 6.50, s, CH.

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

Procedure: A solution of 40 g of methyl undecyl ketone and 18 g of hydroxylamino hydrochloride in 200 ml of ethanol, 60 ml of water and 10 g of NaOH is refluxed for 5 hours and thereafter cooled. The ethanol is distilled off in vacuo and the reaction mixture is then diluted with water, extracted with ether and the ethereal extract is dried over Na2SO4. The ether is distilled off and the solid residue is then distilled in vacuo, affording 40 g of 2-tridecanone oxime. Melting point (after recrystallisation from ether); 51°-53° C. cooled The ethanol is distilled off in vacuo the reaction mixture is then diluted with water extracted with ether the ethereal extract is dried over Na2SO4 The ether is distilled off the solid residue is then distilled in vacuo

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

Procedure: A solution of 40 g of methyl undecyl ketone and 18 g of hydroxylamino hydrochloride in 200 ml of ethanol, 60 ml of water and 10 g of NaOH is refluxed for 5 hours and thereafter cooled. The ethanol is distilled off in vacuo and the reaction mixture is then diluted with water, extracted with ether and the ethereal extract is dried over Na2SO4. The ether is distilled off and the solid residue is then distilled in vacuo, affording 40 g of 2-tridecanone oxime. Melting point (after recrystallisation from ether); 51°-53° C. cooled The ethanol is distilled off in vacuo the reaction mixture is then diluted with water extracted with ether the ethereal extract is dried over Na2SO4 The ether is distilled off the solid residue is then distilled in vacuo

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 70 g of methyl undecyl ketone are added to 250 ml of formamide. The mixture is heated, with constant stirring, to 160° C. Then 40 ml of formic acid are added dropwise in the course of 24 hours. The reaction mixture is cooled, poured on ice, extracted with ether and the ethereal extract is dried over Na2SO4. After distilling off the ether, the oily residue is distilled in vacuo, affording 60 g of 2-formamidotridecane. Boiling point: 145°-155° C./0.01. The reaction mixture is cooled poured on ice extracted with ether the ethereal extract is dried over Na2SO4 After distilling off the ether the oily residue is distilled in vacuo

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

Procedure: A reactor equipped with a stirrer, reflux-condenser, thermometer and nitrogen gas inlet pipe was charged with 297 g of 2-tridecanone, 166 g of glycerol and a solvent amount of toluene, and following addition of p-toluenesulfonic acid as a catalyst, the dehydrative condensation reaction was carried out at the reflux temperature for 24 hours. The resulting crude product was washed with an aqueous solution of potassium carbonate and further with 3 portions of distilled water and finally purified by distillation under reduced pressure to provide 2-methyl-2-undecyl-4-hydroxymethyl-1,3-dioxolane. A reactor equipped with a stirrer, reflux-condenser the dehydrative condensation reaction The resulting crude product was washed with an aqueous solution of potassium carbonate and further with 3 portions of distilled water finally purified by distillation under reduced pressure

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

Procedure: A solution of n-butyllithium (12.6 mL, 27.7 mmol, 2.2 M in hexane) was added dropwise via syringe to a cooled (-78° C.) solution of diisopropylamine (4.1 mL, 29 mmol) in dry THF (200 mL). The resulting solution was stirred (15 minutes -78° C.), then a solution of 2-tridecanone (5.0 g, 25 mmol) in dry THF (50 mL) was added dropwise via a drop-in funnel. The resulting mixture was stirred (30 minutes, -78° C.), then a solution of chlorotrimethylsilane (3.5 mL, 28 mmol) in dry THF (40 mL) was added in one portion. The dry ice bath was removed and the resulting mixture was warmed to 10° C., then quenched with saturated sodium bicarbonate (100 mL). Dichloromethane (400 mL) and water (80 mL) were added and the layers were separated. The organic layer was washed with brine (1×200 mL), dried (MgSO4), and concentrated in vacuo to yield 6.7 g (98%) of the title compound as a milky oil which was used without further purification. The resulting mixture was stirred (30 minutes, -78° C.) The dry ice bath was removed quenched with saturated sodium bicarbonate (100 mL) Dichloromethane (400 mL) and water (80 mL) were added the layers were separated The organic layer was washed with brine (1×200 mL) dried (MgSO4) concentrated in vacuo

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