methyl 5-oxocyclopent-1-ene-1-heptanoate synthesis

13synthesis methods

Product Name:methyl 5-oxocyclopent-1-ene-1-heptanoate
CAS Number:34546-57-1
Molecular formula:C13H20O3
Molecular Weight:224.2961

Dodecanoic acid, 9,12-dioxo-, methyl ester

50266-44-9
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methyl 5-oxocyclopent-1-ene-1-heptanoate

34546-57-1
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Yield:34546-57-1 98%

Reaction Conditions:

with sodium methylate;sodium in methanol;water;

Steps:

8 7-(5-keto-cyclopentenyl)-heptanoic acid, methyl ester (VII)

EXAMPLE 8 7-(5-keto-cyclopentenyl)-heptanoic acid, methyl ester (VII) A solution of the ester (VI) (10 g, 0.041 mole) in methanol (15 ml) is added dropwise, under nitrogen and stirring at reflux, to a solution of sodium methoxide [prepared from sodium (2.17 g; 0.094 mole) and methanol (280 ml)] At the end of the addition, the mixture is refluxed for 15 minutes. The methanol is evaporated and the residue is treated with water/ice, acidified and extracted with methylene chloride (4*25 ml) and washed with water (3*25 ml). After anhydration and evaporation, the residue is taken up with methanol (50 ml) and concentrated hydrochloric acid (1.5 ml). The mixture is stirred at room temperature for 18 hours. The mixture is evaporated, taken up with methylene chloride (50 ml), washed with water (3*20 ml). A crude product is obtained (9 g) which is distilled in a bubble oven at about 0.7 mm/Hg (145°-148° C. (Yield=98%). I.R. (liquid film): 1740, 1705, 1630, 1170 cm^-1. ¹ H-NMR (δ, CDCl₃): 1.35÷2.4 (m, 16H, CH₂); 3.60 (s, 3H, OCH₃) 7.26 (m, 1H, CH=).

References:

US4894473,1990,A