2-methylcyclohex-2-en-1-one

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

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

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of LDA (prepared from BuLi, 1.6 M in hexane, 75 ml, 0.12 mol and diisopropylamine, 12.2 g, 0.12 mol) in THF (50 ml) was added 2-methyl-cyclohex-2-enone (11.0 g, 0.1 mol) at −78° C. The mixture was stirred for 1 h at −78° C. and prenyl bromide 17.88 g, 0.12 mol) was added. The mixture was stirred over night, while the temperature was allowed to rise to room temperature. MTBE (50 ml) and sat. NH4Cl were added, the organic phase was separated and washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was distilled in a Kugelrohr oven to yield 9.8 g (55%) of a slightly yellow oil. The mixture was stirred over night, while the temperature to rise to room temperature the organic phase was separated washed with brine dried (MgSO4) concentrated in vacuo The residue was distilled in a Kugelrohr oven to yield 9.8 g (55%) of a slightly yellow oil

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of LDA (prepared from BuLi, 1.6 M in hexane, 75 ml, 0.12 mol and diisopropylamine, 12.2 g, 0.12 mol) in THF (50 ml) was added 2-methyl-cyclohex-2-enone (11.0 g, 0.1 mol) at −78° C. The mixture was stirred for 1 h at −78° C. and prenyl bromide 17.88 g, 0.12 mol) was added. The mixture was stirred over night, while the temperature was allowed to rise to room temperature. MTBE (50 ml) and sat. NH4Cl were added, the organic phase was separated and washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was distilled in a Kugelrohr oven to yield 9.8 g (55%) of a slightly yellow oil. The mixture was stirred over night, while the temperature to rise to room temperature the organic phase was separated washed with brine dried (MgSO4) concentrated in vacuo The residue was distilled in a Kugelrohr oven to yield 9.8 g (55%) of a slightly yellow oil

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: Benzenesulfinic acid sodium salt (2.9 g) was added to a solution containing 1.5 g of 2-methyl-2-cyclohexen-1-one and 8 ml of water. Then 16 ml of 1N hydrochloric acid was added dropwise to the resulting mixture. The reaction mixture was stirred at room temperature for 24 hours. The crystals so precipitated were filtered and then, washed with water, isopropanol and cold ethyl ether. After recrystallization from isopropanol, 2-methyl-3-(phenylsulfonyl)-cyclohexan-1-one was obtained in the form of white crystals. Yield: 93% The crystals so precipitated were filtered washed with water, isopropanol and cold ethyl ether After recrystallization from isopropanol

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

Procedure: At room temp., 2N aqueous sodium hydroxide (7.00 mL, 14.0 mmol), followed by 30% aqueous hydrogen peroxide (11.0 mL, 112 mmol) was added to a stirred solution of commercially available 2-methylcyclohex-2-enone (2.20 g, 20.0 mmol) in methanol (250 mL), upon which the resulting red color of the solution faded within 10 min. After stirring at room temp. for 24 h, the reaction mixture was diluted with water (200 mL) and extracted with dichloromethane (3×150 mL). The combined organic extracts were washed with water (200 mL) and dried with sodium sulfate. The solvent was removed under reduced pressure, and the resulting residue purified by chromatography on silica gel [40 g; pentane-Et2O (9:1); Rf=0.29] to furnish 1-methyl-7-oxabicyclo[4.1.0]heptan-2-one (1.18 g, 47%) as a colourless liquid. At room temp. extracted with dichloromethane (3×150 mL) The combined organic extracts were washed with water (200 mL) dried with sodium sulfate The solvent was removed under reduced pressure the resulting residue purified by chromatography on silica gel [40 g; pentane-Et2O (9:1); Rf=0.29]

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

Procedure: Benzenesulfinic acid sodium salt (2.9 g) was added to a solution containing 1.5 g of 2-methyl-2-cyclohexen-1-one and 8 ml of water. Then 16 ml of 1N hydrochloric acid was added dropwise to the resulting mixture. The reaction mixture was stirred at room temperature for 24 hours. The crystals so precipitated were filtered and then, washed with water, isopropanol and cold ethyl ether. After recrystallization from isopropanol, 2-methyl-3-(phenylsulfonyl)-cyclohexan-1-one was obtained in the form of white crystals. Yield: 93%, TLC: (hexane-AcOEt: 6-4) Rf=0.25 The crystals so precipitated were filtered washed with water, isopropanol and cold ethyl ether After recrystallization from isopropanol

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of LDA (prepared from BuLi, 1.6 M in hexane, 75 ml, 0.12 mol and diisopropylamine, 12.2 g, 0.12 mol) in THF (50 ml) was added 2-methyl-cyclohex-2-enone (11.0 g, 0.1 mol) at −78° C. The mixture was stirred for 1 h at −78° C. and prenyl bromide 17.88 g, 0.12 mol) was added. The mixture was stirred over night, while the temperature was allowed to rise to room temperature. MTBE (50 ml) and sat. NH4Cl were added, the organic phase was separated and washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was distilled in a Kugelrohr oven to yield 9.8 g (55%) of a slightly yellow oil. The mixture was stirred over night, while the temperature to rise to room temperature the organic phase was separated washed with brine dried (MgSO4) concentrated in vacuo The residue was distilled in a Kugelrohr oven to yield 9.8 g (55%) of a slightly yellow oil