2-hexylcyclopent-2-en-1-one

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

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

Procedure: In a 2-L flask fitted with a reflux condenser, is placed 332 g of 2-n-hexyl-2-cyclopentenone, 183 g of nitromethane, 30 ml of 40% methanolic solution of benzyltrimethylammonium hydroxide (Triton B) and 200 ml of dry dioxane. The reaction mixture is refluxed for 23 hours. The solvent is distilled off under a reduced pressure and the residue is dissolved in 1 L of ether. The ether solution is washed successively with dilute hydrochloric acid, water and sodium bicarbonate solution and dried over anhydrous sodium sulphate. The solvent is removed at atmospheric pressure and the residue is distilled through a short Vigreux column. After a lower boiling fraction (35 g, 65° C/0.2 mm) consisting of 2-n-hexyl-2-cyclopentenone, the product is collected at 135° C/0.3 mm, yield 365 g (80%), nD20 1.4733. In a 2-L flask fitted with a reflux condenser The reaction mixture is refluxed for 23 hours The solvent is distilled off under a reduced pressure the residue is dissolved in 1 L of ether The ether solution is washed successively with dilute hydrochloric acid, water and sodium bicarbonate solution dried over anhydrous sodium sulphate The solvent is removed at atmospheric pressure the residue is distilled through a short Vigreux column After a lower boiling fraction (35 g, 65° C/0.2 mm) the product is collected at 135° C/0.3 mm, yield 365 g (80%)

Conditions: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 3-L three necked flask fitted with a mechanical stirrer, a reflux condenser, a dropping funnel and a thermometer, are placed 83 g of 2-n-hexyl-cyclopentenone, 1.75 L 95% ethyl alcohol and 30 g of glacial acetic acid. The mixtures is warmed up with sirring to 35° C and a solution of 65 g of potassium cyanide in 190 ml of water is added over a period of 15 minutes. Stirring is continued for 3 hours, the temperature being maintained at 35° C. The methanol is then distilled off at a reduced pressure the organic layer is separated, and the water phase is extracted with ether. The combined organic layer and ether extract are washed with sodium carbonate solution and water and dried over anhydrous sodium sulphate. The solvent is removed at atmospheric pressure and the residue is distilled through a short Vigreux column. 2-n-Hexyl-3-cyanocyclopentanone is collected at 106°-110° C/0,2 mm, yield 85 g (88%), nD 20 1.4658. the temperature being maintained at 35° C The methanol is then distilled off at a reduced pressure the organic layer is separated the water phase is extracted with ether The combined organic layer and ether extract are washed with sodium carbonate solution and water dried over anhydrous sodium sulphate The solvent is removed at atmospheric pressure the residue is distilled through a short Vigreux column 2-n-Hexyl-3-cyanocyclopentanone is collected at 106°-110° C/0,2 mm, yield 85 g (88%), nD 20 1.4658

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

Procedure: A mixture of 16,6 g of 2-n-hexyl-2-cyclopentenone (see foot note (1) under Table II) 12 g of acetone cyanhydrine (Org. Synth. Coll. Vol.2, p.7), 32 ml of methanol and 0.8 g of sodium carbonate in 12 ml of water, is heated at reflux temperature for 11/2 hours. is heated at reflux temperature for 11/2 hours

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

Procedure: In a 2-L flask fitted with a reflux condenser, is placed 332 g of 2-n-hexyl-2-cyclopentenone, 183 g of nitromethane, 30 ml of 40% methanolic solution of benzyltrimethylammonium hydroxide (Triton B) and 200 ml of dry dioxane. The reaction mixture is refluxed for 23 hours. The solvent is distilled off under a reduced pressure and the residue is dissolved in 1 L of ether. The ether solution is washed successively with dilute hydrochloric acid, water and sodium bicarbonate solution and dried over anhydrous sodium sulphate. The solvent is removed at atmospheric pressure and the residue is distilled through a short Vigreux column. After a lower boiling fraction (35 g, 65°C/0.2 mm) consisting of 2-n-hexyl-2-cyclopentenone, the product is collected at 135°C/0.3 mm, yield 365 g (80%), nD20 1.4733. In a 2-L flask fitted with a reflux condenser The reaction mixture is refluxed for 23 hours The solvent is distilled off under a reduced pressure the residue is dissolved in 1 L of ether The ether solution is washed successively with dilute hydrochloric acid, water and sodium bicarbonate solution dried over anhydrous sodium sulphate The solvent is removed at atmospheric pressure the residue is distilled through a short Vigreux column After a lower boiling fraction (35 g, 65°C/0.2 mm) the product is collected at 135°C/0.3 mm, yield 365 g (80%)

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

Procedure: In a 2-L flask fitted with a reflux condenser, is placed 332 g of 2-n-hexyl-2-cyclopentenone, 183 g of nitromethane, 30 ml of 40% methanolic solution of benzyltrimethylammonium hydroxide (Triton B) and 200 ml of dry dioxane. The reaction mixture is refluxed for 23 hours. The solvent is distilled off under a reduced pressure and the residue is dissolved in 1 L of ether. The ether solution is washed successively with dilute hydrochloric acid, water and sodium bicarbonate solution and dried over anhydrous sodium sulphate. The solvent is removed at atmospheric pressure and the residue is distilled through a short Vigreux column. After a lower boiling fraction (35 g, 65°C/0.2 mm) consisting of 2-n-hexyl-2-cyclopentenone, the product is collected at 135°C/0.3 mm, yield 365 g (80%), nD20 1.4733. In a 2-L flask fitted with a reflux condenser The reaction mixture is refluxed for 23 hours The solvent is distilled off under a reduced pressure the residue is dissolved in 1 L of ether The ether solution is washed successively with dilute hydrochloric acid, water and sodium bicarbonate solution dried over anhydrous sodium sulphate The solvent is removed at atmospheric pressure the residue is distilled through a short Vigreux column After a lower boiling fraction (35 g, 65°C/0.2 mm) the product is collected at 135°C/0.3 mm, yield 365 g (80%)

Conditions: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 3-L three necked flask fitted with a mechanical stirrer, a reflux condenser, a dropping funnel and a thermometer, are placed 83 g of 2-n-hexyl-cyclopentenone, 1.75 L 95% ethyl alcohol and 30 g of glacial acetic acid. The mixture is warmed up with sirring to 35°C and a solution of 65 g of potassium cyanide in 190 ml of water is added over a period of 15 minutes. Stirring is continued for 3 hours, the temperature being maintained at 35°C. The methanol is then distilled off at a reduced pressure the organic layer is separated, and the water phase is extracted with ether. The combined organic layer and other extract are washed with sodium carbonate solution and water and dried over anhydrous sodium sulphate. The solvent is removed at atmospheric pressure and the residue is distilled through a short Vigreux column. 2-n-Hexyl-3-cyanocyclopentanone is collected at 106°-110°C/0,2 mm, yield 85 g (88%), nD20 1.4658. the temperature being maintained at 35°C The methanol is then distilled off at a reduced pressure the organic layer is separated the water phase is extracted with ether The combined organic layer and other extract are washed with sodium carbonate solution and water dried over anhydrous sodium sulphate The solvent is removed at atmospheric pressure the residue is distilled through a short Vigreux column 2-n-Hexyl-3-cyanocyclopentanone is collected at 106°-110°C/0,2 mm, yield 85 g (88%)

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

Procedure: A mixture of 16,6 g of 2-n-hexyl-2-cyclopentenone (see foot note (1) under Table II) 12 g of acetone cyanhydrine (Org.Synth.Coll. Vol. 2, p. 7), 32 ml of methanol and 0,8 g of sodium carbonate in 12 ml of water, is heated at reflux temperature for 31/2 hours. is heated at reflux temperature for 31/2 hours

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

Procedure: The above prepared mixture (25 parts) was admixed with p-toluenesulfonic acid (1.25 parts) and toluene (75 parts) and refluxed for 2 hours, during which by-produced water was eliminated by azeotropic distillation. The reaction mixture was treated as in Example 1 to give 2-n-hexyl-2-cyclopentenone in a yield of 97 %. The above prepared mixture (25 parts) refluxed for 2 hours, during which was eliminated by azeotropic distillation The reaction mixture was treated as in Example 1

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

Procedure: In a 2-L flask fitted with a reflux condenser, is placed 332 g of 2-n-hexyl-2-cyclopentenone, 183 g of nitromethane, 30 ml of 40% methanolic solution of benzyltrimethylammonium hydroxide (Triton B) and 200 ml of dry dioxane. The reaction mixture is refluxed for 23 hours. The solvent is distilled off under a reduced pressure and the residue is dissolved in 1 L of ether. The ether solution is washed successively with dilute hydrochloric acid, water and sodium bicarbonate solution and dried over anhydrous sodium sulphate. The solvent is removed at atmospheric pressure and the residue is distilled through a short Vigreux column. After a lower boiling fraction (35 g, 65° C/0.2 mm) consisting of 2-n-hexyl-2-cyclopentenone, the product is collected at 135° C/0.3 mm, yield 365 g (80%), nD20 1.4733. In a 2-L flask fitted with a reflux condenser The reaction mixture is refluxed for 23 hours The solvent is distilled off under a reduced pressure the residue is dissolved in 1 L of ether The ether solution is washed successively with dilute hydrochloric acid, water and sodium bicarbonate solution dried over anhydrous sodium sulphate The solvent is removed at atmospheric pressure the residue is distilled through a short Vigreux column After a lower boiling fraction (35 g, 65° C/0.2 mm) the product is collected at 135° C/0.3 mm, yield 365 g (80%)

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

Procedure: In a 2-L flask fitted with a reflux condenser, is placed 332 g of 2-n-hexyl-2-cyclopentenone, 183 g of nitromethane, 30 ml of 40% methanolic solution of benzyltrimethylammonium hydroxide (Triton B) and 200 ml of dry dioxane. The reaction mixture is refluxed for 23 hours. The solvent is distilled off under a reduced pressure and the residue is dissolved in 1 L of ether. The ether solution is washed successively with dilute hydrochloric acid, water and sodium bicarbonate solution and dried over anhydrous sodium sulphate. The solvent is removed at atmospheric pressure and the residue is distilled through a short Vigreux column. After a lower boiling fraction (35 g, 65° C/0.2 mm) consisting of 2-n-hexyl-2-cyclopentenone, the product is collected at 135° C/0.3 mm, yield 365 g (80%), nD20 1.4733. In a 2-L flask fitted with a reflux condenser The reaction mixture is refluxed for 23 hours The solvent is distilled off under a reduced pressure the residue is dissolved in 1 L of ether The ether solution is washed successively with dilute hydrochloric acid, water and sodium bicarbonate solution dried over anhydrous sodium sulphate The solvent is removed at atmospheric pressure the residue is distilled through a short Vigreux column After a lower boiling fraction (35 g, 65° C/0.2 mm) the product is collected at 135° C/0.3 mm, yield 365 g (80%)

Conditions: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 3-L three necked flask fitted with a mechanical stirrer, a reflux condenser, a dropping funnel and a thermometer, are placed 83 g of 2-n-hexyl-cyclopentenone, 1.75 L 95% ethyl alcohol and 30 g of glacial acetic acid. The mixtures is warmed up with sirring to 35° C and a solution of 65 g of potassium cyanide in 190 ml of water is added over a period of 15 minutes. Stirring is continued for 3 hours, the temperature being maintained at 35° C. The methanol is then distilled off at a reduced pressure the organic layer is separated, and the water phase is extracted with ether. The combined organic layer and ether extract are washed with sodium carbonate solution and water and dried over anhydrous sodium sulphate. The solvent is removed at atmospheric pressure and the residue is distilled through a short Vigreux column. 2-n-Hexyl-3-cyanocyclopentanone is collected at 106°-110° C/0,2 mm, yield 85 g (88%), nD 20 1.4658. the temperature being maintained at 35° C The methanol is then distilled off at a reduced pressure the organic layer is separated the water phase is extracted with ether The combined organic layer and ether extract are washed with sodium carbonate solution and water dried over anhydrous sodium sulphate The solvent is removed at atmospheric pressure the residue is distilled through a short Vigreux column 2-n-Hexyl-3-cyanocyclopentanone is collected at 106°-110° C/0,2 mm, yield 85 g (88%), nD 20 1.4658