methyl 9-oxooctadecanoate

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3 grams of the C8H17CH(CO2H)2 product obtained above were added, in small portions, to a mixture of 3.3 ml dihydropyran in 25 ml of benzene and 20 μl sulfuric acid, and stirred at 25° C., for 1 hour. Potassium hydroxide was added to neutralize the sulfuric acid, and the mixture was stirred for an additional 30 minutes. The solvent was then evaporated and, with 25 ml benzene, the mixture was added dropwise to NaH in 30 ml benzene, and stirred for 1 hour. 3 g of the CH3OCO(CH2)7COCl product prepared above was added dropwise and the mixture stirred overnight. Acetic acid (0.3 ml) was added and the mixture refluxed for 4 hours. The residue was taken up in ether, washed with 1N NaOH, water and brine, and dried. Chromatography on silica gel with 15% ethylacetate and hexane gave 1.5 g of C8H17CH2CO(CH2)7COOCH3. the mixture was stirred for an additional 30 minutes The solvent was then evaporated and, with 25 ml benzene the mixture was added dropwise to NaH in 30 ml benzene stirred for 1 hour 3 g of the CH3OCO(CH2)7COCl product prepared above was added dropwise the mixture stirred overnight the mixture refluxed for 4 hours washed with 1N NaOH, water and brine dried

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3 grams of the C8H17CH(CO2H)2 product obtained above were added, in small portions, to a mixture of 3.3 ml dihydropyran in 25 ml of benzene and 20 μl sulfuric acid, and stirred at 25° C., for 1 hour. Potassium hydroxide was added to neutralize the sulfuric acid, and the mixture was stirred for an additional 30 minutes. The solvent was then evaporated and, with 25 ml benzene, the mixture was added dropwise to NaH in 30 ml benzene, and stirred for 1 hour. 3 g of the CH3OCO(CH2)7COCl product prepared above was added dropwise and the mixture stirred overnight. Acetic acid (0.3 ml) was added and the mixture refluxed for 4 hours. The residue was taken up in ether, washed with 1N NaOH, water and brine, and dried. Chromatography on silica gel with 15% ethylacetate and hexane gave 1.5 g of C8H17CH2CO(CH2)7COOCH3. the mixture was stirred for an additional 30 minutes The solvent was then evaporated and, with 25 ml benzene the mixture was added dropwise to NaH in 30 ml benzene stirred for 1 hour 3 g of the CH3OCO(CH2)7COCl product prepared above was added dropwise the mixture stirred overnight the mixture refluxed for 4 hours washed with 1N NaOH, water and brine dried