2-ethylcyclohexan-1-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: 2-Ethylcyclohexanol (1.6 moles, 204 g, 226 mL) was stirred in 3.2 l of acetone at 0° C. and treated with 8N Jones reagent (prepared from 106.8 g of CrO3 suspended in 92 mL of concentrated sulfuric acid and diluted to 400 mL with water) until the orange color persisted (~430 mL). Isopropanol was then added to turn the solution green again after which it was poured into 2 l of ether. The product was washed with 6×500 ml of brine, dried over MgSO4 and stripped of solvent. Short path distillation (b.p. 80°-85° C. at 25 mm) afforded 184 g (1.46 moles, 91%) of 2-ethylcyclohexanone as a colorless oil. The product was washed with 6×500 ml of brine dried over MgSO4 Short path distillation (b.p. 80°-85° C. at 25 mm)

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

Procedure: 2-Ethylcyclohexanol (1.6 moles, 204 g, 226 mL) was stirred in 3.2 l of acetone at 0° C. and treated with 8N Jones reagent (prepared from 106.8 g of CrO3 suspended in 92 mL of concentrated sulfuric acid and diluted to 400 mL with water) until the orange color persisted (~430 mL). Isopropanol was then added to turn the solution green again after which it was poured into 2 l of ether. The product was washed with 6×500 ml of brine, dried over MgSO4 and stripped of solvent. Short path distillation (b.p. 80°-85° C. at 25 mm) afforded 184 g (1.46 moles, 91%) of 2-ethylcyclohexanone as a colorless oil. The product was washed with 6×500 ml of brine dried over MgSO4 Short path distillation (b.p. 80°-85° C. at 25 mm)

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

Procedure: A solution of 2-ethylcyclohexanone (6.92 mol, 873 g), (R)-α-methylbenzylamine (6.92 mol, 839 g), and 19.6 mL of acetic acid were refluxed for 12 hours under nitrogen in 2 L of toluene with azeotropic removal of water. The toluene was removed on a rotary evaporator and the product was divided into two portions. The unreacted 2-ethylcyclohexanone was distilled through a short path (bp 30° C., <10 mm), and the remainder of the product was then distilled through a 5" vacuum jacketed Vigreux column affording first a low melting solid (bp 80°-90° C. 23 mm), and then the product (bp 128°-133° C. 21.0 mm, 1.303 kg from both distillations combined, 5.68 mol, 82%). The toluene was removed on a rotary evaporator The unreacted 2-ethylcyclohexanone was distilled through a short path (bp 30° C., <10 mm) the remainder of the product was then distilled through a 5" vacuum affording first a low melting solid (bp 80°-90° C. 23 mm)

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

Procedure: A solution of 2-ethylcyclohexanone (6.92 mol, 873 g), (R)-α-methylbenzylamine (6.92 mol, 839 g), and 19.6 mL of acetic acid were refluxed for 12 hours under nitrogen in 2 L of toluene with azeotropic removal of water. The toluene was removed on a rotary evaporator and the product was divided into two portions. The unreacted 2-ethylcyclohexanone was distilled through a short path (bp 30° C., <10 mm), and the remainder of the product was then distilled through a 5" vacuum jacketed Vigreux column affording first a low melting solid (bp 80°-90° C. 23 mm), and then the product (bp 128°-133° C. 21.0 mm, 1.303 kg from both distillations combined, 5.68 mol, 82%). The toluene was removed on a rotary evaporator The unreacted 2-ethylcyclohexanone was distilled through a short path (bp 30° C., <10 mm) the remainder of the product was then distilled through a 5" vacuum affording first a low melting solid (bp 80°-90° C. 23 mm)

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

Procedure: 2-Ethylcyclohexanol (1.6 moles, 204 g, 226 mL) was stirred in 3.2 L of acetone at 0° C. and treated with 8N Jones reagent (prepared from 106.8 g of CrO3 suspended in 92 mL of concentrated sulfuric acid and diluted to 400 mL with water) until the orange color persisted (~430 mL). Isopropanol was then added to turn the solution green again after which it was poured into 2 L of ether. The product was washed with 6×500 mL of brine, dried over MgSO4 and stripped of solvent. Short path distillation (b.p. 80°-85° C. at 25 mm) afforded 184 g (1.46 moles, 91%) of 2-ethylcyclohexanone as a colorless oil. The product was washed with 6×500 mL of brine dried over MgSO4 Short path distillation (b.p. 80°-85° C. at 25 mm)

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

Procedure: 2-Ethylcyclohexanol (1.6 moles, 204 g, 226 mL) was stirred in 3.2 L of acetone at 0° C. and treated with 8N Jones reagent (prepared from 106.8 g of CrO3 suspended in 92 mL of concentrated sulfuric acid and diluted to 400 mL with water) until the orange color persisted (~430 mL). Isopropanol was then added to turn the solution green again after which it was poured into 2 L of ether. The product was washed with 6×500 mL of brine, dried over MgSO4 and stripped of solvent. Short path distillation (b.p. 80°-85° C. at 25 mm) afforded 184 g (1.46 moles, 91%) of 2-ethylcyclohexanone as a colorless oil. The product was washed with 6×500 mL of brine dried over MgSO4 Short path distillation (b.p. 80°-85° C. at 25 mm)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-ethylcyclohexanone (104.3 mmol) in water and ethanol, and sodium acetate (125.1 mmol) were added hydroxylamine hydrochloride (156.4 mmol), the reaction was heated at 70° C. overnight. The ethanol was removed under reduced pressure, and the reaction mixture was dissolved in water. The aqueous layer was extracted with ether, and the combined organic extracts were washed with brine, dried over sodium sulfate, and concentrated to give 2-ethyl-1-(hydroxyimino)cyclohexane (52%) as a thick oil. The ethanol was removed under reduced pressure the reaction mixture was dissolved in water The aqueous layer was extracted with ether the combined organic extracts were washed with brine dried over sodium sulfate concentrated

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-ethylcyclohexanone (104.3 mmol) in water and ethanol, and sodium acetate (125.1 mmol) were added hydroxylamine hydrochloride (156.4 mmol), the reaction was heated at 70° C. overnight. The ethanol was removed under reduced pressure, and the reaction mixture was dissolved in water. The aqueous layer was extracted with ether, and the combined organic extracts were washed with brine, dried over sodium sulfate, and concentrated to give 2-ethyl-1-(hydroxyimino)cyclohexane (52%) as a thick oil. The ethanol was removed under reduced pressure the reaction mixture was dissolved in water The aqueous layer was extracted with ether the combined organic extracts were washed with brine dried over sodium sulfate concentrated

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-ethylcyclohexanone (104.3 mmol) in water and ethanol, and sodium acetate (125.1 mmol) were added hydroxylamine hydrochloride (156.4 mmol), the reaction was heated at 70° C. overnight. The ethanol was removed under reduced pressure, and the reaction mixture was dissolved in water. The aqueous layer was extracted with ether, and the combined organic extracts were washed with brine, dried over sodium sulfate, and concentrated to give 2-ethyl-1-(hydroxyimino)cyclohexane (52%) as a thick oil. The ethanol was removed under reduced pressure the reaction mixture was dissolved in water The aqueous layer was extracted with ether the combined organic extracts were washed with brine dried over sodium sulfate concentrated

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

Procedure: 2-Ethylcyclohexanol (1.6 moles, 204 g, 226 ml) was stirred in 3.2 l of acetone at 0° C. and treated with 8N Jones reagent (prepared from 106.8 g of CrO3 suspended in 92 ml of concentrated sulfuric acid and diluted to 400 ml with water) until the orange color persisted (~430 ml). Isopropanol was then added to turn the solution green again after which it was poured into 2 l of ether. The product was washed with 6×500 ml of brine, dried over MgSO4 and stripped of solvent. Short path distillation (b.p. 80°-85° C. at 25 mm) afforded 184 g (1.46 moles, 91%) of 2-ethylcyclohexanone as a colorless oil. The product was washed with 6×500 ml of brine dried over MgSO4 Short path distillation (b.p. 80°-85° C. at 25 mm)