4-methoxycyclohexan-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:

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

Procedure: To 2.5 g of ethyl acetate was added 1.12 g of 60% sodium hydride and, a solution of 1.78 g of 4-methoxycyclohexanone in benzene was added to the mixture. After reacting at 40° C. for 3 hours, methanol was added to decompose an excess of sodium hydride, which was poured into water. The mixture was neutralized with hydrochloric acid ahd extracted with ether to give 1.02 g of 2-acetyl-4-methoxycyclohexanone. ahd extracted with ether

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

Procedure: To a suspension of 60% sodium hydride (1.12 g) in 2.5 g of ethyl acetate, a solution consisting of 1.78 g of 4-methoxycyclohexanone and 0.5 ml of benzene was dropwise added. The reaction was allowed to proceed at 40° C. for 3 hours and then at room temperature for 3 hours. A small amount of methanol was added to decompose the sodium hydride. The reaction mixture was then poured into water, neutralized with hydrochloric acid, and extracted with ether. Thus, 1.16 g of 2-acetyl-4-methoxycyclohexanone was obtained. was dropwise added at room temperature for 3 hours extracted with ether

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

Procedure: To a suspension of 60% sodium hydride (1.12 g) in 2.5 g of ethyl acetate, a solution consisting of 1.78 g of 4-methoxycyclohexanone and 0.5 ml of benzene was dropwise added. The reaction was allowed to proceed at 40° C. for 3 hours and then at room temperature for 3 hours. A small amount of methanol was added to decompose the sodium hydride. The reaction mixture was then poured into water, neutralized with hydrochloric acid, and extracted with ether. Thus, 1.16 g of 2-acetyl-4-methoxycyclohexanone was obtained. was dropwise added at room temperature for 3 hours extracted with ether

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

Procedure: To methylene chloride there was added 11 g of pyridinium chlorochromate, and a solution consisting of 4.2 g of 4-methoxycyclohexanol and 30 ml of methylene chloride was then added. The reaction was carried out at room temperature for 3 hours. The product was purified on Florisil column. After distillation, there was obtained 3.7 g of 4-methoxycyclohexanone. was then added The product was purified on Florisil column After distillation

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

Procedure: 4-Methoxycyclohexanol (2.0 g, 15.0 mmol) was taken up in 150 mL of DCM. Pyridinium chlorochromate (5.0 g, 23.0 mmol) was added. After 60 hours, the mixture was filtered through a plug of Florisil and concentrated under reduced pressure. The residue was taken up in 50 mL of ether and filtered through a plug of silica gel. The solvent was removed under reduced pressure, affording 4-methoxycyclohexanone as a light yellow oil. the mixture was filtered through a plug of Florisil concentrated under reduced pressure filtered through a plug of silica gel The solvent was removed under reduced pressure

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

Procedure: The procedure of Example I was repeated, but the p-methoxyphenol was used in molten form without addition of methylcyclohexane. After a hydrogenation time of 380 minutes, 62.1% by weight of the p-methoxyphenol had reacted and p-methoxycyclohexanone had been formed in a yield of 46.5% by weight.

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

Procedure: The procedure of Example I was repeated, but the p-methoxyphenol was used in molten form without addition of methylcyclohexane. After a hydrogenation time of 380 minutes, 62.1% by weight of the p-methoxyphenol had reacted and p-methoxycyclohexanone had been formed in a yield of 46.5% by weight.

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

Procedure: 0.5 g of borax and 0.5 g of water were mixed and 6 g of a catalyst which was moist with water (water content=50 %) and comprised 5% by weight of palladium on carbon were then mixed in. The resulting mixture was added to a solution of 100 g of p-methoxyphenol in 150 g of methylcyclohexane and this reaction mixture was hydrogenated in a stirred reactor at from 150 to 180° C. and from 3 to 8 bar of hydrogen pressure until no more hydrogen was absorbed. After a hydrogenation time of 72 minutes, 96.2% by weight of the p-methoxyphenol had reacted and p-methoxycyclohexanone had been formed in a yield of 83% by weight. were then mixed in was absorbed After a hydrogenation time of 72 minutes, 96.2% by weight of the p-methoxyphenol had reacted

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

Procedure: To a stirred suspension of sodium hydride (60% in mineral oil, 1.20 g, 30.0 mmol) in dimethylsulfoxide (19 mL) was added trimethylsulfoxonium iodide (6.89 g, 31.3 mmol) at room temperature, and the mixture was stirred at room temperature for 30 min. To this mixture was added a solution of 4-methoxycyclohexanone (3.53 g, 10.0 mmol, prepared according to Shvily, Ronit et al., J. Chem. Soc. Perkin Trans. 2, 1997, 6, 1221) in dimethylsulfoxide (95 mL) dropwise at room temperature, and the mixture was stirred at room temperature for 20 h. Then the mixture was diluted with water (1.0 L), and extracted with diethyl ether (200 mL×6). The combined organic layers were dried over magnesium sulfate, and concentrated in vacuo. The residue was chromatographed on a column of silica gel eluting n-hexane/ethyl acetate (v/v=15/1˜10/1) to give 338 mg (9%, cis) and 204 mg (5%, trans) of the title compound as colorless oil respectively. prepared extracted with diethyl ether (200 mL×6) The combined organic layers were dried over magnesium sulfate concentrated in vacuo The residue was chromatographed on a column of silica gel eluting n-hexane/ethyl acetate (v/v=15/1˜10/1)