cyclodecanone

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: 0.5 g (2.7 mmol) of 1-vinyl-1-cyclodecanol (cf. I.1.3, comprises also about 8-10% cyclodecanone), quartz reactor 25/400 mm, temperature 670° C.±10, vaporization at 95-100° C. (airbath temperature) in about 10 min. Nitrogen stream about 2-2.5 l/h, vacuum 5-6 mbar. 0.45 g (90% crude yield) of a pure white condensate were obtained which partially crystallized into small fine needles. According to GC and GC/MS analyses, the mixture comprises, as main component, about 70% cyclododecanone, as well as 6-8% cyclodecanone and 2-3% starting material. Chromatographic separation of the mixture over silica gel (hexane/TBME 97:3) gave 0.26 g of cyclododecanone (52% isolated yield), which has identical retention times and spectroscopic properties as the commercially available compound (Fluka). 400 mm, temperature 670° C. at 95-100° C. in about 10 min 0.45 g (90% crude yield) of a pure white condensate were obtained which partially crystallized into small fine needles Chromatographic separation of the mixture over silica gel (hexane/TBME 97:3)

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

Procedure: 0.5 g (2.7 mmol) of 1-vinyl-1-cyclodecanol (cf. I.1.3, comprises also about 8-10% cyclodecanone), quartz reactor 25/400 mm, temperature 670° C.±10, vaporization at 95-100° C. (airbath temperature) in about 10 min. Nitrogen stream about 2-2.5 l/h, vacuum 5-6 mbar. 0.45 g (90% crude yield) of a pure white condensate were obtained which partially crystallized into small fine needles. According to GC and GC/MS analyses, the mixture comprises, as main component, about 70% cyclododecanone, as well as 6-8% cyclodecanone and 2-3% starting material. Chromatographic separation of the mixture over silica gel (hexane/TBME 97:3) gave 0.26 g of cyclododecanone (52% isolated yield), which has identical retention times and spectroscopic properties as the commercially available compound (Fluka). 400 mm, temperature 670° C. at 95-100° C. in about 10 min 0.45 g (90% crude yield) of a pure white condensate were obtained which partially crystallized into small fine needles Chromatographic separation of the mixture over silica gel (hexane/TBME 97:3)

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

Procedure: A mixture of 1.40 grams (10 millimoles) of cyclodecane, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide, 0.015 gram (0.06 millimole) of Co(AA)2 and 25 milliliters of acetic acid was stirred in an oxygen atmosphere at a temperature of 100° C. for six hours. As a result, cyclodecane was transformed into cyclodecanone (yield 39%), sebacic acid (yield 48%) and cyclodecanedione (yield 5%) with a transformation rate of 96%.

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

Procedure: A mixture of 25.0 g of cyclodecanone, 60.7 g of diethyl aminomethylenemalonate, 1.54 g of p-toluenesulfonic acid monohydrate in 500 ml xylene is refluxed 2 weeks under argon, collecting the distillate in a Dean-Stark trap. The solution is then decanted and solvent is removed. The residual oil is triturated twice with hexane and the combined hexane extract is concentrated to yield an oil which is flash chromatographed on 600 g of silica gel using 99:1 methylene chloride ethyl acetate as eluent. A forerun containing cyclodecanone is discarded and the fractions containing the product are combined and concentrated to dryness to give diethyl N-(1-cyclodecenyl)-aminomethylenemalonate as an oil. is refluxed 2 weeks under argon collecting the distillate in a Dean-Stark trap The solution is then decanted solvent is removed The residual oil is triturated twice with hexane the combined hexane extract is concentrated to yield an oil which chromatographed on 600 g of silica gel using 99:1 methylene chloride ethyl acetate as eluent A forerun containing cyclodecanone the fractions containing the product concentrated to dryness

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

Procedure: 0.5 g (2.7 mmol) of 1-vinyl-1-cyclodecanol (cf. I.1.3, comprises also about 8-10% cyclodecanone), quartz reactor 25/400 mm, temperature 670° C.±10, vaporization at 95-100° C. (airbath temperature) in about 10 min. Nitrogen stream about 2-2.5 l/h, vacuum 5-6 mbar. 0.45 g (90% crude yield) of a pure white condensate were obtained which partially crystallized into small fine needles. According to GC and GC/MS analyses, the mixture comprises, as main component, about 70% cyclododecanone, as well as 6-8% cyclodecanone and 2-3% starting material. Chromatographic separation of the mixture over silica gel (hexane/TBME 97:3) gave 0.26 g of cyclododecanone (52% isolated yield), which has identical retention times and spectroscopic properties as the commercially available compound (Fluka). 400 mm, temperature 670° C. at 95-100° C. in about 10 min 0.45 g (90% crude yield) of a pure white condensate were obtained which partially crystallized into small fine needles Chromatographic separation of the mixture over silica gel (hexane/TBME 97:3)

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclodecanone (n=6) (1.0 g) in 10 mL concentrated sulfuric acid was cooled to 0° C. and 0.54 g of sodium azide was added. The reaction continued to stir at 0° C. for 1 h and warmed to room temperature where it was stirred for two h. The solution was diluted with cold water and treated with cold 10% NaOH solution until pH=9. Extraction with ether (2×), drying over magnesium sulfate and evaporation of solvent provided 1.23 g of 2-azacycloundecanone. warmed to room temperature where it was stirred for two h Extraction with ether (2×) drying over magnesium sulfate and evaporation of solvent

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

Procedure: A mixture of 1.40 grams (10 millimoles) of cyclodecane, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide, 0.015 gram (0.06 millimole) of Co(AA)2 and 25 milliliters of acetic acid was stirred in an oxygen atmosphere at a temperature of 100° C. for six hours. As a result, cyclodecane was transformed into cyclodecanone (yield 39%), sebacic acid (yield 48%) and cyclodecanedione (yield 5%) with a transformation rate of 96%.