Acetic Acid → 3,5-Dimethyldodecanoic acid

Reaktionsgleichung

[CH3:1][CH:2]([CH:13](C([O-])=O)[C:14]([O:16]CC)=[O:15])[CH2:3][CH:4]([CH3:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C(O)(=O)C.S(=O)(=O)(O)O>O>[CH3:1][CH:2]([CH2:3][CH:4]([CH3:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:13][C:14]([OH:16])=[O:15]

Komponenten

Versuchsvorschrift

In a nitrogen atmosphere, ethyl 2-(1,3-dimethyldecyl)malonate (4Et) (18.6 g, 0.0566 mol), acetic acid (40 g), water (20 g), and sulfuric acid (2 g) were placed in a reaction vessel and stirred for 48 hours under refluxing with heating while distilling off ethanol. The reaction mixture was diluted with tetrahydrofuran and water. The organic phase was washed with an aqueous saturated sodium chloride solution and concentrated under reduced pressure. The concentrate thus obtained was distilled under reduced pressure (bp: from 130° C. to 140° C./2 mmHg) to obtain 3,5-dimethyldodecanoic acid (5) (11.4 g, 0.0498 mol). A total yield of three steps from the 2-methylnonyl chloride (1Cl) was 59%.