ChemicalBook CAS DataBase List Undecanedioic acid

Undecanedioic acid synthesis

6synthesis methods

Product Name:Undecanedioic acid
CAS Number:1852-04-6
Molecular formula:C11H20O4
Molecular Weight:216.27

Undecanedioic acid is obtained by reacting α -nitro ketone and NaOH in MeOH.To a solution of α -nitro ketone (0.7 mmol) in MeOH (4.2 ml), 25 ml of 0.5 M Na2HPO4 in a 1 N of NaOH were added and the resulting mixture was heated at 70 °C for 1-4 h, then Oxone (1.75 mmol) in water (3 ml) was added to the cold solution (r. t.). After 4 h the mixture was diluted with brine (10 ml), acidified to pH=2 with a 10% solution of HCl and extracted with EtOAc (3 x 20 ml). The combined organic layers were washed with brine (10 ml), dried over Na2SO4 and evaporated to yield pure dicarboxylic acid.
synthetic method of Undecanedioic acid

Fig The synthetic method 2 of Undecanedioic acid.

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Yield:1852-04-6 100 %Chromat.

Reaction Conditions:

with hydrogen

Steps:

1

EXAMPLE 1; This example illustrates the synthesis of the C₁₁diacid starting from oleic acid. In a first stage, the ethenolysis of oleic acid is carried out at 30° C. in the presence of a tungsten-based catalyst in order to obtain 9-decenoic acid CH₂CH-(CH₂)₇-COOH. For the second stage, use is made of the bispyridine ruthenium complex (8) catalyst described in the publication by Chen-Xi Bei et al., Tetrahedron Letters, 46 (2005), 7225-7228, in carrying out the cross-metathesis of 9-decenoic acid with methyl acrylate. The reaction is carried out in CH₂Cl₂, at a 0.1M 9-decenoic acid concentration and a 0.2M methyl acrylate concentration, at a temperature of 50° C. and for 12 hours. The yields are determined by chromatographic analysis. In the present case, use is made of 2 equivalents of methyl acrylate with respect to the acid and with a catalyst concentration of 0.5 mol %. The yield of product CH₃-OOC-CHCH-(CH₂)₇-COOH is 50 mol %. This product can be hydrogenated according to a conventional process with a yield of 100%.

References:

US2010/305354,2010,A1 Location in patent:Page/Page column 6

201230-82-2 Synthesis