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ChemicalBook CAS DataBase List Dimethyl azelate
1732-10-1

Dimethyl azelate synthesis

11synthesis methods
-

Yield:1731-84-6 71% ，1732-10-1 70% ，18824-63-0 14% ，1599-48-0 13%

Reaction Conditions:

Stage #1:methanol;cis-Octadecenoic acid with oxygen;ozone at 0 - 20;
Stage #2: with semicarbazide hydrochloride in methanol at 0;Solvent;Reagent/catalyst;

Steps:

Ozonolysis of oleic acid (1). General procedure
General procedure: At ozone generator output 40 mmol O3/h through a solution of 1.41 g (5.0 mmol) of oleic acid 1 in 25 mL of anhydrous alcohol or 20 mL of anhydrous THF or 25 mL of a mixture AcOH-CH2Cl2, 1 : 5, at 0 °C was bubbled ozone-oxygen mixture till 5.5 mmol of ozone was consumed. The reaction mixture was flushed with argon and then it was treated by two procedures. a. At 0 °C 1.20 g (17.3 mmol) of NH2OH·HCl was added, the mixture was stirred at room temperature till disappearance of peroxides (iodine-starch test). The solvent was distilled off, the residue was dissolved in CHCl3 (50 mL), the obtained solution was washed with H2O (2 × 15 mL), dried over Na2SO4, and evaporated. Ozonolysis in methanol. By method b after chromatographing 1.85 g of residue (SiO2, petroleum ether-tert-butyl methyl ether, 2 : 1) we obtained 0.61 g (71%) of methyl nonanoate 5, 0.13 g (14%) of 1,1-dimethoxynonane 9, 0.76 g (70%) of dimethyl nonanedioate 7, and 0.16 g (13%) of methyl 9,9-dimethoxynonanoate 10. Methyl nonanoate (5). Rf 0.59 (petroleum ether-tert-butyl methyl ether, 2 : 1). IR, H1 and C13 NMR spectra are identic to those previously described [16, 17]. Dimethyl nonanedioate (7). Rf 0.45 (petroleum ether-tert-butyl methyl ether, 2 : 1). IR, 1H and 13C NMR spectra are identic to those previously described [17]. 1,1-Dimethoxynonane (9). Rf 0.62 (petroleum ether-tert-butyl methyl ether, 2 : 1). 1H NMR spectrum is identic to that previously described [19]. Methyl 9,9-dimethoxynonanoate (10). Rf 0.47 (petroleum ether-tert-butyl methyl ether, 2 : 1). IR, 1H and 13C NMR spectra are identic to those previously described [20].

References:

Ishmuratov, G. Yu.;Yakovleva;Botsman;Legostaeva, Yu. V.;Nazarov;Baidimirov [Russian Journal of Organic Chemistry,2015,vol. 51,# 5,p. 610 - 614]

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