dodecanedial

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

Procedure: The above reaction was repeated, but 15-(dimethylphosphono)-pentadec-12-en-14-on-1-al was replaced by a mixture of 0.79 g (4 mMole) of dodecan-1,12-dial and 1.10 g (4 mMole) of 1,3-bis(dimethylphosphono)-propan-2-one in 10 ml of 90% t-butanol. Identical introduction time and work up gave 229 mg (26%) of cyclopentadeca-2,14-dien-1-one in a similar ratio of isomers. The above reaction

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

Procedure: A solution of 5 g of potassium bicarbonate in 150 ml of water was added to a mixture of 8.22 g (30 mMole) of 1,3-bis(dimethylphosphono)propan-2-one and 5.94 g (80 mMole) of dodecan-1,12-dial in 150 ml of t-butanol. After 21/2 h stirring at 27° under nitrogen water was added and the mixture was extracted with ether. The organic layer was separated, washed with brine, dried over sodium sulphate and evaporated. The residue was chromatographed on 150 g of silica gel. Hexane-ethyl acetate 1:1 eluted 2.68 g of unreacted dodecan-1,12-dial and ether eluted 4.38 g (42%, resp. 75% when based on recovered dial) of the title compound as a viscous oil. was added the mixture was extracted with ether The organic layer was separated washed with brine dried over sodium sulphate evaporated The residue was chromatographed on 150 g of silica gel Hexane-ethyl acetate 1:1 eluted 2.68 g of unreacted dodecan-1,12-dial and ether eluted 4.38 g (42%, resp. 75% when based on recovered dial) of the title compound as a viscous oil

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

Procedure: The above reaction was repeated, but 15-(dimethylphosphono)-pentadec-12-en-14-on-1-al was replaced by a mixture of 0.79 g (4 mMole) of dodecan-1,12-dial and 1.10 g (4 mMole) of 1,3-bis(dimethylphosphono)-propan-2-one in 10 ml of 90% t-butanol. Identical introduction time and work up gave 229 mg (26%) of cyclopentadeca-2,14-dien-1-one in a similar ratio of isomers. The above reaction

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

Procedure: A solution of 5 g of potassium bicarbonate in 150 ml of water was added to a mixture of 8.22 g (30 mMole) of 1,3-bis(dimethylphosphono)propan-2-one and 5.94 g (80 mMole) of dodecan-1,12-dial in 150 ml of t-butanol. After 21/2 h stirring at 27° under nitrogen water was added and the mixture was extracted with ether. The organic layer was separated, washed with brine, dried over sodium sulphate and evaporated. The residue was chromatographed on 150 g of silica gel. Hexane-ethyl acetate 1:1 eluted 2.68 g of unreacted dodecan-1,12-dial and ether eluted 4.38 g (42%, resp. 75% when based on recovered dial) of the title compound as a viscous oil. was added the mixture was extracted with ether The organic layer was separated washed with brine dried over sodium sulphate evaporated The residue was chromatographed on 150 g of silica gel Hexane-ethyl acetate 1:1 eluted 2.68 g of unreacted dodecan-1,12-dial and ether eluted 4.38 g (42%, resp. 75% when based on recovered dial) of the title compound as a viscous oil

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 162.3 g (1 mol) of cyclododecatriene (purity 95%) were dissolved in 1500 ml of methanol, the solution was cooled to -20° C., and an O3 /O2 mixture containing 4% by weight of O3 was passed in until 0.33 mol of ozone had been introduced into the solution. The hydrogenation solution obtained as in Example 1 contained dodecanedial and its acetals. Cyclododecane formed was extracted from the acetic acid solution using petroleum ether prior to the oxidation. had been introduced into the solution

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 162.3 g (1 mol) of cyclododecatriene (purity 95%) were dissolved in 1500 ml of methanol, the solution was cooled to -20° C., and an O3 /O2 mixture containing 4% by weight of O3 was passed in until 0.33 mol of ozone had been introduced into the solution. The hydrogenation solution obtained as in Example 1 contained dodecanedial and its acetals. Cyclododecane formed was extracted from the acetic acid solution using petroleum ether prior to the oxidation. had been introduced into the solution

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 162.3 g (1 mol) of cyclododecatriene (purity 95%) were dissolved in 1500 ml of methanol, the solution was cooled to -20° C., and an O3 /O2 mixture containing 4% by weight of O3 was passed in until 0.33 mol of ozone had been introduced into the solution. The hydrogenation solution obtained as in Example 1 contained dodecanedial and its acetals. Cyclododecane formed was extracted from the acetic acid solution using petroleum ether prior to the oxidation. had been introduced into the solution

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

Procedure: The above reaction was repeated, but 15-(dimethylphosphono)-pentadec-12-en-14-on-1-al was replaced by a mixture of 0.79 g (4 mMole) of dodecan-1,12-dial and 1.10 g (4 mMole) of 1,3-bis(dimethylphosphono)-propan-2-one in 10 ml of 90% t-butanol. Identical introduction time and work up gave 229 mg (26%) of cyclopentadeca-2,14-dien-1-one in a similar ratio of isomers The above reaction

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

Procedure: A solution of 5 g of potassium bicarbonate in 150 ml of water was added to a mixture of 8.22 g (30 mMole) of 1,3-bis(dimethylphosphono)propan-2-one and 5.94 g (30 mMole) of dodecan-1,12-dial in 150 ml of t-butanol. After 21/2 h stirring at 27° under nitrogen water was added and the mixture was extracted with ether. The organic layer was separated, washed with brine, dried over sodium sulphate and evaporated. The residue was chromatographed on 150 g of silica gel. Hexane-ethyl acetate 1:1 eluted 2.68 g of unreacted dodecan-1,12-dial and ether eluted 4.38 g (42%, resp. 76% when based on recovered dial) of the title compound as a viscous oil. was added the mixture was extracted with ether The organic layer was separated washed with brine dried over sodium sulphate evaporated The residue was chromatographed on 150 g of silica gel Hexane-ethyl acetate 1:1 eluted 2.68 g of unreacted dodecan-1,12-dial and ether eluted 4.38 g (42%, resp. 76% when based on recovered dial) of the title compound as a viscous oil

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

Procedure: The above reaction was repeated, but 15-(dimethylphosphono)-pentadec-12-en-14-on-1-al was replaced by a mixture of 0.79 g (4 mMole) of dodecan-1,12-dial and 1.10 g (4 mMole) of 1,3-bis(dimethylphosphono)-propan-2-one in 10 ml of 90% t-butanol. Identical introduction time and work up gave 229 mg (26%) of cyclopentadeca-2,14-dien-1-one in a similar ratio of isomers. The above reaction

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

Procedure: A solution of 5 g of potassium bicarbonate in 150 ml of water was added to a mixture of 8.22 g (30 mMole) of 1,3-bis(dimethylphosphono)propan-2-one and 5.94 g (80 mMole) of dodecan-1,12-dial in 150 ml of t-butanol. After 21/2 h stirring at 27° under nitrogen water was added and the mixture was extracted with ether. The organic layer was separated, washed with brine, dried over sodium sulphate and evaporated. The residue was chromatographed on 150 g of silica gel. Hexane-ethyl acetate 1:1 eluted 2.68 g of unreacted dodecan-1,12-dial and ether eluted 4.38 g (42%, resp. 75% when based on recovered dial) of the title compound as a viscous oil. was added the mixture was extracted with ether The organic layer was separated washed with brine dried over sodium sulphate evaporated The residue was chromatographed on 150 g of silica gel Hexane-ethyl acetate 1:1 eluted 2.68 g of unreacted dodecan-1,12-dial and ether eluted 4.38 g (42%, resp. 75% when based on recovered dial) of the title compound as a viscous oil