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Sodium Hydroxide → 3,5-Dimethyldodecanoic acid

HRID 922092
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 922092
[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].[OH-].[Na+]>>[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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

3

Edukt 2

HCID 14798Sodium HydroxideHCID 131734962HCID 131734962, Verbindung

Produkt 1

HCID 569358013,5-Dimethyldodecanoic acid

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

In a nitrogen atmosphere, the crude product (41.6 g, 0.0899 mol) of ethyl 2-(1,3-dimethyldecyl)malonate (4Et) obtained in the method of Example 1-1 and a 13% by weight aqueous sodium hydroxide solution (87 g) were placed in a reaction vessel and stirred for one hour under refluxing with heating. Then ethanol thus generated therein was distilled off in one hour. The resulting mixture was subjected to addition of 20% by weight hydrochloric acid (87 g) and extracted with a mixture of toluene and tetrahydrofuran. The resulting organic phase was concentrated under reduced pressure, and then the residue was stirred under heat at 170° C. for 6 hours in a nitrogen atmosphere. This reaction mixture was diluted with tetrahydrofuran, washed with an aqueous saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The concentrate thus obtained was distilled under reduced pressure (bp 130 to 140° C./2 mmHg) to obtain 3,5-dimethyldodecanoic acid (5) (18.9 g, 0.0828 mol). A total yield of three steps from the 2-methylnonyl chloride (1Cl) was 67%.

Aufarbeitung

  1. temperatureunder refluxing
  2. temperaturewith heating
  3. distillationThen ethanol thus generated therein was distilled off in one hour
  4. additionThe resulting mixture was subjected to addition of 20% by weight hydrochloric acid (87 g)
  5. extractionextracted with a mixture of toluene and tetrahydrofuran
  6. concentrationThe resulting organic phase was concentrated under reduced pressure
  7. stirringthe residue was stirred
  8. additionThis reaction mixture was diluted with tetrahydrofuran
  9. washwashed with an aqueous saturated sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. concentrationThe concentrate thus
  13. customobtained
  14. distillationwas distilled under reduced pressure (bp 130 to 140° C./2 mmHg)

Quellen und Nachweise

ORD-Eintrag
ord-b3d2401952ff4266b88aedd44f04cd1d
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09278900B2

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