Methyl acetoacetate → Methyl 2-acetyloctanoate

HRID 5619

Reaktionsgleichung

Reaktionsgleichung von HRID 5619
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C[O-].[Na+].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>CO>[C:3]([CH:2]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:1]([O:7][CH3:8])=[O:6])(=[O:4])[CH3:5]

Komponenten

5

Edukt 3

HCID 7757Methyl acetoacetateHCID 81011-BromohexaneHCID 10942334Sodium Methoxide

Produkt 1

HCID 3390996Methyl 2-acetyloctanoateAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

465 g of methyl acetoacetate were added dropwise under nitrogen and stirring to 720 g of 30% sodium methylate solution in 1200 ml of methanol. Then, 727 g of 1-bromohexane were added and the reaction mixture was boiled at reflux for 20 hours. The majority of the methanol was distilled off and the residue was poured on to ice-water. The mixture was extracted with n-hexane and then with water. The organic phases were combined and dried over sodium sulphate. The solvent was evaporated and the crude ester was distilled. There were obtained 499.4 g of methyl 2-acetyloctanoate, b.p. 124°-128°/15 Torr.

Aufarbeitung

  1. temperatureat reflux for 20 hours
  2. distillationThe majority of the methanol was distilled off
  3. additionthe residue was poured on to ice-water
  4. extractionThe mixture was extracted with n-hexane
  5. dry with materialdried over sodium sulphate
  6. customThe solvent was evaporated
  7. distillationthe crude ester was distilled

Quellen und Nachweise

ORD-Eintrag
ord-fabc61b31cd147d983caa87d8e7474d5
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245056

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