Sodium Hydroxide → Methyl 4-oxodecanoate

HRID 599714

Reaktionsgleichung

Reaktionsgleichung von HRID 599714
[O:1]=[C:2]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][CH2:4][C:5]([O:7][CH2:8]C(C)C)=[O:6].[OH-].[Na+]>CO>[O:1]=[C:2]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 252092612-Methylpropyl 4-oxodecanoate

Produkt 1

HCID 538627Methyl 4-oxodecanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To the resulting isobutyl 4-oxodecanoate were added 1 L of methanol and 250 g of 25% sodium hydroxide, and the mixture was stirred at 25° C. for 1 hour, followed by distilling off methanol in vacuo. Subsequently, thereto were added 2 L of water and 1 L of toluene. The resulting mixture was stirred at room temperature for 1 hour and then allowed to stand to separate the water phase. To the water phase were added 175 g of concentrated hydrochloric acid and 1.8 L of toluene. The resulting mixture was stirred for 10 minutes and then allowed to stand to separate the organic phase. Toluene in the organic phase was distilled off in vacuo and 1 L of toluene and 47.5 mL of concentrated sulfuric acid were added. The resulting mixture was heated under reflux for 1 hour and then cooled to 25° C. Thereto was gradually added 155 g of sodium hydrogencarbonate followed by stirring for 10 minutes at 25° C. Methanol was distilled off in vacuo and then 3 L of water and 1.8 L of toluene were added. The resulting mixture was stirred for 10 minutes at room temperature and then allowed to stand to separate the organic phase. Toluene in the organic phase was distilled off, yielding methyl 4-oxodecanoate (a compound in which R17 represents an n-pentyl group, and R18 represents a methyl group in the above formula (12)). Gas chromatographic analysis showed that the yield of methyl 4-oxodecanoate relative to isobutyl 4-oxodecanoate was 95%.

Aufarbeitung

  1. distillationby distilling off methanol in vacuo
  2. additionSubsequently, thereto were added 2 L of water and 1 L of toluene
  3. stirringThe resulting mixture was stirred at room temperature for 1 hour
  4. customto separate the water phase
  5. additionTo the water phase were added 175 g of concentrated hydrochloric acid and 1.8 L of toluene
  6. stirringThe resulting mixture was stirred for 10 minutes
  7. customto separate the organic phase
  8. distillationToluene in the organic phase was distilled off in vacuo and 1 L of toluene and 47.5 mL of concentrated sulfuric acid
  9. additionwere added
  10. temperatureThe resulting mixture was heated
  11. temperatureunder reflux for 1 hour
  12. temperaturecooled to 25° C
  13. stirringby stirring for 10 minutes at 25° C
  14. distillationMethanol was distilled off in vacuo
  15. addition3 L of water and 1.8 L of toluene were added
  16. stirringThe resulting mixture was stirred for 10 minutes at room temperature
  17. customto separate the organic phase
  18. distillationToluene in the organic phase was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-0535824467e640658d22b42a72a705c0
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897802B2

Verknüpfte Notizen

Wird geladen…