2-[(4-methoxyphenyl)methylidene]cyclohexan-1-one

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 22.68 g (0.252 moles) of N-methoxycarbonyl hydrazine in 100 ml of benzene a solution of 50.0 g (0.23 moles) of 2-(p-methoxyphenylmethylene)-cyclohexan-1-one in 300 ml of anhydrous methanol is added, under stirring. The reaction mixture is boiled for one hour, clarified with activated carbon, filtered and the filtrate is cooled. 63.05 g of the desired compound are obtained. Yield: 94.65%. filtered the filtrate is cooled

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 22.68 g (0.252 moles) of N-methoxycarbonyl hydrazine in 100 ml of benzene a solution of 50.0 g (0.23 moles) of 2-(p-methoxyphenylmethylene)-cyclohexan-1-one in 300 ml of anhydrous methanol is added, under stirring. The reaction mixture is boiled for one hour, clarified with activated carbon, filtered and the filtrate is cooled. 63.05 g of the desired compound are obtained. Yield: 94.65%. filtered the filtrate is cooled

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 22.68 g (0.252 moles) of N-methoxycarbonyl hydrazine in 100 ml of benzene a solution of 50.0 g (0.23 moles) of 2-(p-methoxyphenylmethylene)-cyclohexan-1-one in 300 ml of anhydrous methanol is added, under stirring. The reaction mixture is boiled for one hour, clarified with activated carbon, filtered and the filtrate is cooled. 63.05 g of the desired compound are obtained. Yield: 94.65%. filtered the filtrate is cooled

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:180.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 100-ml, four-necked flask equipped with a mechanical stirrer, a reflux condenser and a thermometer were placed 21.6 g (0.1 mole) of the 2-(4-methoxybenzylidene)cyclohexanone produced in Example 8 and 51.7 g (0.3 mole) of diethyl maleate in this order. The flask inside was purged with nitrogen. Thereto was added 2.2 g (10 wt. %, 1.0 mmole as palladium) of 5% palladium carbon (a product of Wako Pure Chemical Industries, Ltd.). The mixture was stirred at 180° C. for 6 hours and cooled to room temperature. 200 ml of toluene was added to the system. Filtration was conducted to remove the palladium carbon. The filtrate was extracted with 150 ml of a 7% aqueous sodium hydroxide solution, and this operation was repeated twice. The aqueous layer was washed with 50 ml of toluene. To the resulting aqueous layer was added 35% hydrochloric acid until the aqueous layer became acidic, after which the aqueous layer was extracted with 150 ml of ethyl acetate. The ethyl acetate layer was washed with water and a saturated aqueous sodium chloride solution in this order. The ethyl acetate layer was dried over anhydrous sodium sulfate and then subjected to vacuum distillation to remove ethyl acetate, to obtain 13.3 g of light yellow crystals. Yield: 62% The purity of the intended product in the crystals was 97% as measured by high performance liquid chromatography. In a 100-ml, four-necked flask equipped with a mechanical stirrer, a reflux condenser The flask inside was purged with nitrogen cooled to room temperature Filtration to remove the palladium carbon The filtrate was extracted with 150 ml of a 7% aqueous sodium hydroxide solution The aqueous layer was washed with 50 ml of toluene To the resulting aqueous layer was added 35% hydrochloric acid until the aqueous layer after which the aqueous layer was extracted with 150 ml of ethyl acetate The ethyl acetate layer was washed with water The ethyl acetate layer was dried over anhydrous sodium sulfate subjected to vacuum distillation to remove ethyl acetate

反応条件: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 1,000-ml, four-necked flask equipped with a mechanical stirrer, a reflux condenser and a thermometer were placed 68 g (0.5 mole) of p-anisaldehyde, 147 g (1.5 moles) of cyclohexanone and then 200 ml of water slowly. Thereto was slowly added, in a water bath, an aqueous solution obtained by diluting 80 g (0.5 mole) of a 25% aqueous sodium hydroxide solution, with 300 ml of water. The system was stirred at 65° C. for 48 hours and cooled to room temperature. To the system were added 400 ml of toluene and 100 ml of water for phase separation. The aqueous layer was re-extracted with 100 ml of toluene. The toluene layers were combined and washed with water and a saturated aqueous sodium chloride solution in this order. The resulting toluene layer was dried over anhydrous sodium sulfate and subjected to vacuum distillation to remove toluene and the excessive (remaining) cyclohexanone. To the crude oil obtained were added 80 ml of toluene and 80 ml of n-hexane for recrystallization, to obtain 80.4 g of yellow crystals. Yield: 74% The purity of the intended product in the crystals was 88% as measured by high performance liquid chromatography. In a 1,000-ml, four-necked flask equipped with a mechanical stirrer, a reflux condenser Thereto was slowly added, in a water bath an aqueous solution obtained cooled to room temperature for phase separation The aqueous layer was re-extracted with 100 ml of toluene washed with water The resulting toluene layer was dried over anhydrous sodium sulfate subjected to vacuum distillation to remove toluene To the crude oil obtained for recrystallization

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 22.68 g (0.252 moles) of N-methoxycarbonyl hydrazine in 100 ml of benzene a solution of 50.0 g (0.23 moles) of 2-(p-methoxyphenylmethylene)-cyclohexan-1-one in 300 ml of anhydrous methanol is added, under stirring. The reaction mixture is boiled for one hour, clarified with activated carbon, filtered and the filtrate is cooled. 63.05 g of the desired compound are obtained. Yield: 94.65%. filtered the filtrate is cooled