hexan-3-one

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

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

Procedure: Kirk-Othmer i.b.i.d. discloses that unsymmetrical dialkyl ketones are prepared by passing vapors of two different fatty acids over an alkaline earth oxide at elevated temperatures. It is stated that the product necessarily contains the three possible ketones and in the example given a mixture of acetic acid and butyric acid are reacted in the vapor phase at 300° C. on a manganese dioxide catalyst to produce 16% methyl ethyl ketone, 24% propyl butyl ketone and 60% ethyl propyl ketone. are prepared

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4 ml (31 mmol) of n-hexane, 0.03 mmol of 4-dodecyloxycarbonyl-N-hydroxyphthalimide, 0.0003 mmol of acetylacetonatocobalt(II) and 0.003 mmol of manganese(II) acetate was stirred at 100° C. in an atmosphere of air (10 atm=1 MPa) for 2 hours and thereby yielded 0.1 mmol of 2-hexanone, 0.09 mmol of 2-hexanol, 0.04 mmol of 3-hexanone and 0.05 mmol of 3-hexanol.

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

Procedure: Kirk-Othmer i.b.i.d. discloses that unsymmetrical dialkyl ketones are prepared by passing vapors of two different fatty acids over an alkaline earth oxide at elevated temperatures. It is stated that the product necessarily contains the three possible ketones and in the example given a mixture of acetic acid and butyric acid are reacted in the vapor phase at 300° C. on a manganese dioxide catalyst to produce 16% methyl ethyl ketone, 24% propyl butyl ketone and 60% ethyl propyl ketone. are prepared

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (0.108 g, 0.500 mmol), 3-hexanone (2.0 mL), p-toluenesulfonic acid monohydrate (0.0095 g, 0.050 mmol) and acetic acid (2.0 mL) was stirred overnight at 80° C. in a sealed tube. The mixture was poured into sat. aqueous sodium hydrogen carbonate (150 mL). Extraction with ethyl acetate (100 mL), drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil. This oil was purified by column chromatography (Combiflash, 12 g silica gel, dichloromethane to 90:10 dichloromethane/methanol), then recrystallized from methanol, and the precipitate was collected by filtration. This yellow solid contained methanol, so it was stirred in ethyl acetate (5.0 mL) for 30 min at 70° C. After cooling, the precipitate was collected by filtration to afford the title compound (0.0334 g, 22%) as a yellow solid: Extraction with ethyl acetate (100 mL) drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil This oil was purified by column chromatography (Combiflash, 12 g silica gel, dichloromethane to 90:10 dichloromethane/methanol) recrystallized from methanol the precipitate was collected by filtration so it was stirred in ethyl acetate (5.0 mL) for 30 min at 70° C After cooling the precipitate was collected by filtration

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4 ml (31 mmol) of n-hexane, 0.03 mmol of 4-dodecyloxycarbonyl-N-hydroxyphthalimide, 0.0003 mmol of acetylacetonatocobalt(II) and 0.003 mmol of manganese(II) acetate was stirred at 100° C. in an atmosphere of air (10 atm=1 MPa) for 2 hours and thereby yielded 0.1 mmol of 2-hexanone, 0.09 mmol of 2-hexanol, 0.04 mmol of 3-hexanone and 0.05 mmol of 3-hexanol.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4 ml (31 mmol) of n-hexane, 0.03 mmol of 4-dodecyloxycarbonyl-N-hydroxyphthalimide, 0.0003 mmol of acetylacetonatocobalt(II) and 0.003 mmol of manganese(II) acetate was stirred at 100° C. in an atmosphere of air (10 atm=1 MPa) for 2 hours and thereby yielded 0.1 mmol of 2-hexanone, 0.09 mmol of 2-hexanol, 0.04 mmol of 3-hexanone and 0.05 mmol of 3-hexanol.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4 ml (31 mmol) of n-hexane, 0.03 mmol of 4-dodecyloxycarbonyl-N-hydroxyphthalimide, 0.0003 mmol of acetylacetonatocobalt(II) and 0.003 mmol of manganese(II) acetate was stirred at 100° C. in an atmosphere of air (10 atm=1 MPa) for 2 hours and thereby yielded 0.1 mmol of 2-hexanone, 0.09 mmol of 2-hexanol, 0.04 mmol of 3-hexanone and 0.05 mmol of 3-hexanol.

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The operating conditions are substantially those of example 29: 0.236 mole of 1-hexene (30 cc), 65 cc of anhydrous isopropanol, 2 millimoles of palladium chloride, 4 millimoles of Cu (ClO4)2 (HMPT)4 complex and 5 cc water are introduced into a heat-insulated reactor and stirred at 40° C at a pH of about 7. After 4 hours of reaction, 25 millimoles of oxygen is absorbed; 25 millimoles of 2-hexanone (selectivity: 41%) and 12 millimoles of 3-hexanone (selectivity: 20%) is formed; 60 millimoles of 1-hexene is consumed. Thus, not only the activity is low but it is found that a mixture of two ketones is formed, instead of only 2-hexanone as in example 29. is absorbed

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

Procedure: A solution of 1-(2-amino-4-methoxycarbonylphenyl)-5,5-bis-(hydroxymethyl)pyrrolidin-2-one (0.15 g, 0.51 mmol) from Example 6 in 1 mL of dichloromethane and 0.5 mL of acetic acid was treated with 3-hexanone (0.3 g, 3 mmol) and sodium cyanoborohydride (0.1 g, 1.6 mmol). The resulting mixture was stirred at ambient temperature for 6 h after which time additional 3-hexanone (0.1 g, 1 mmol), sodium cyanoborohydride (0.05 g, 0.8 mmol) and methanol (0.5 mL) were added. Stirring was continued for 12 h. A third portion of 3-hexanone (0.17 g, 1.7 mmol) and sodium cyanoborohydride (0.055 g, 0.9 mmol) was added and stirring continued for an additional 16 h. The reaction mixture was quenched with 10 mL of a saturated sodium bicarbonate solution and extracted with ethyl acetate (3×50 mL). The combined extracts were dried and concentrated. The residue was purified by chromatography (silica gel; 5% ethanol in ether) to give 0.175 g (90%) of 1-[2-(3-hexylamino)-4-methoxycarbonylphenyl]-5,5-bis-(hydroxymethyl)pyrrolidin-2-one as an oil. were added stirring continued for an additional 16 h The reaction mixture was quenched with 10 mL of a saturated sodium bicarbonate solution extracted with ethyl acetate (3×50 mL) The combined extracts were dried concentrated The residue was purified by chromatography (silica gel; 5% ethanol in ether)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4 ml (31 mmol) of n-hexane, 0.03 mmol of 4-dodecyloxycarbonyl-N-hydroxyphthalimide, 0.0003 mmol of acetylacetonatocobalt(II) and 0.003 mmol of manganese(II) acetate was stirred at 100° C. in an atmosphere of air (10 atm=1 MPa) for 2 hours and thereby yielded 0.1 mmol of 2-hexanone, 0.09 mmol of 2-hexanol, 0.04 mmol of 3-hexanone and 0.05 mmol of 3-hexanol.