ChemicalBook CAS DataBase List methyl 3-oxooctadecanoate

methyl 3-oxooctadecanoate synthesis

10synthesis methods

Product Name:methyl 3-oxooctadecanoate
CAS Number:14531-34-1
Molecular formula:C19H36O3
Molecular Weight:312.49

38330-80-2 Synthesis

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Yield:14531-34-1 79%

Reaction Conditions:

Stage #1: monomethyl monopotassium malonatewith triethylamine;magnesium chloride in acetonitrile at 10 - 25; for 2.5 h;Inert atmosphere;
Stage #2: n-hexadecanoyl chloridewith triethylamine in acetonitrile at 0 - 25;Inert atmosphere;

Steps:

All 3-oxo-fatty acid methyl ester were prepared according to Clay et al.

General procedure: In brief: 32.80 g methyl potassium malonate (0.21 mol) was placed in a 1l flask under an Ar blanket. 300 ml MeCN was added and the mixture stirred and cooled to 10-15 °C. To this mixture 44.36 ml dry Et3N (32.40 g, 0.32 mol) was added followed by 23.81 g anhydrous MgCl2 (0.25 mol) and stirring continued at 20-25 °C for 2.5 h. The resulting slurry was recooled to 0 °C and the respective acid chloride (0.1 mol) added dropwise over 25min followed by the addition of 3 ml Et3N. The mixture was allowed to stir over night at 20-25 °C and then concentrated in vacuum to remove the MeCN. The residue was suspended in100 ml toluene and the resulting sludge reconcentrated in vacuum. Again 150 ml toluene was added and the mixture cooled to 10-15 °C. 150 ml aqueous HCl (13%) was added cautiously while keeping the temperature below 25 °C. The aqueous layer was separated and the organic layer washed twice with 40 ml of 13% aq. HCl and 40 ml water. The solution was then concentrated in vacuum to give the crude product which was purified by distillation or recrystallisation. The purity was checked by HPLC/MS.

References:

Sieben, Daniela;Santana, Alexander;Nowka, Paul;Weber, Sven;Funke, Kai;Hüttenhain, Stefan H. [Tetrahedron Letters,2016,vol. 57,# 7,p. 808 - 810] Location in patent:supporting information