methyl 3-oxodecanoate

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 500 ml of toluene was dissolved 160 g (0.8 mol) of the resulting methyl 3-oxodecanoate, the solution was cooled to 0 to 5° C., and 108 g (0.8 mol) of sulfuryl chloride was added thereto dropwise, followed by stirring at room temperature overnight. Toluene was removed by evaporation to give 187.8 g (0.8 mol; yield: 100% from methyl 3-oxodecanoate) of the title compound. Toluene was removed by evaporation

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 500 ml of toluene was dissolved 160 g (0.8 mol) of the resulting methyl 3-oxodecanoate, the solution was cooled to 0 to 5° C., and 108 g (0.8 mol) of sulfuryl chloride was added thereto dropwise, followed by stirring at room temperature overnight. Toluene was removed by evaporation to give 187.8 g (0.8 mol; yield: 100% from methyl 3-oxodecanoate) of the title compound. Toluene was removed by evaporation

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

Procedure: A dry tetrahydrofuran suspension (4 l) containing 440 g (11 mol) of 60% sodium hydride was cooled to 0° C., and 1.8 l of a tetrahydrofuran solution of 1.161 kg (10 mol) of methyl acetoacetate was added thereto dropwise, followed by stirring at room temperature for 1 hour. To the reaction mixture was added dropwise 1.789 kg (11 mol) of octanoyl chloride at 0 to 5° C., followed by stirring at room temperature overnight. After confirming disappearance of the octanoyl chloride by thin layer chromatography (TLC), tetrahydrofuran was evaporated, and the residue was poured into ice-water and extracted with 8 l of ethyl acetate. Ethyl acetate was evaporated, and the residue was poured into a mixture of 400 g of a 28% methanol solution of sodium methoxide and 1.2 e of methanol and heated at 60 to 65° C. for 6 hours while stirring to conduct deacylation. The product was cooled with ice, adjusted to pH 5 with a 10% sulfuric acid aqueous solution, and extracted with ethyl acetate. The ethyl acetate layer was washed successively with a 5% sodium carbonate aqueous solution and a saturated sodium chloride aqueous solution. The ethyl acetate was evaporated, and the concentrated residue was distilled under reduced pressure to give 1.10 kg (5.5 mol; yield: 50%) of methyl 3-oxodecanoate (boiling point: 121° C./5 mmHg). by stirring at room temperature overnight was evaporated the residue was poured into ice-water extracted with 8 l of ethyl acetate Ethyl acetate was evaporated the residue was poured into a mixture of 400 g of a 28% methanol solution of sodium methoxide and 1.2 e of methanol heated at 60 to 65° C. for 6 hours while stirring The product was cooled with ice extracted with ethyl acetate The ethyl acetate layer was washed successively with a 5% sodium carbonate aqueous solution The ethyl acetate was evaporated the concentrated residue was distilled under reduced pressure

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 500 ml of toluene was dissolved 160 g (0.8 mol) of the resulting methyl 3-oxodecanoate, the solution was cooled to 0 to 5° C., and 108 g (0.8 mol) of sulfuryl chloride was added thereto dropwise, followed by stirring at room temperature overnight. Toluene was removed by evaporation to give 187.8 g (0.8 mol; yield: 100% from methyl 3-oxodecanoate) of the title compound. Toluene was removed by evaporation

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

Procedure: A dry tetrahydrofuran suspension (4 l) containing 440 g (11 mol) of 60% sodium hydride was cooled to 0° C., and 1.8 l of a tetrahydrofuran solution of 1.161 kg (10 mol) of methyl acetoacetate was added thereto dropwise, followed by stirring at room temperature for 1 hour. To the reaction mixture was added dropwise 1.789 kg (11 mol) of octanoyl chloride at 0 to 5° C., followed by stirring at room temperature overnight. After confirming disappearance of the octanoyl chloride by thin layer chromatography (TLC), tetrahydrofuran was evaporated, and the residue was poured into ice-water and extracted with 8 l of ethyl acetate. Ethyl acetate was evaporated, and the residue was poured into a mixture of 400 g of a 28% methanol solution of sodium methoxide and 1.2 e of methanol and heated at 60 to 65° C. for 6 hours while stirring to conduct deacylation. The product was cooled with ice, adjusted to pH 5 with a 10% sulfuric acid aqueous solution, and extracted with ethyl acetate. The ethyl acetate layer was washed successively with a 5% sodium carbonate aqueous solution and a saturated sodium chloride aqueous solution. The ethyl acetate was evaporated, and the concentrated residue was distilled under reduced pressure to give 1.10 kg (5.5 mol; yield: 50%) of methyl 3-oxodecanoate (boiling point: 121° C./5 mmHg). by stirring at room temperature overnight was evaporated the residue was poured into ice-water extracted with 8 l of ethyl acetate Ethyl acetate was evaporated the residue was poured into a mixture of 400 g of a 28% methanol solution of sodium methoxide and 1.2 e of methanol heated at 60 to 65° C. for 6 hours while stirring The product was cooled with ice extracted with ethyl acetate The ethyl acetate layer was washed successively with a 5% sodium carbonate aqueous solution The ethyl acetate was evaporated the concentrated residue was distilled under reduced pressure