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Sodium Hydroxide → Ethyl 8-acetyl-12-hydroxy-12-methylheptadecanoate

HRID 372897
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 372897
[C:1]([CH:4]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:3])[CH3:2].[OH-:26].[Na+].[BH4-].[Na+]>O.O1CCCC1>[C:1]([CH:4]([CH2:16][CH2:17][CH2:18][C:19]([OH:26])([CH3:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 14798Sodium Hydroxide2×HCID 4311764Sodium borohydrideHCID 54103623HCID 54103623, Verbindung

Produkt 1

HCID 20322206Ethyl 8-acetyl-12-hydroxy-12-methylheptadecanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

Mercuric acetate (3.8 g., 0.012 mole) is dissolved in water (12 ml.) and tetrahydrofuran (20 ml.) is added to give a suspension of a yellow solid. Then, ethyl 8-acetyl-12-methyl-11-heptadecenoate (4.2 g., 0.012 mole) in tetrahydrofuran (20 ml.) is added, and the mixture stirred at room temperature for 24 hours. After 6 hours, the yellow suspended solid has disappeared and a cloudy solution results. To the solution is added 3M sodium hydroxide solution (12 ml.), followed by 0.5M sodium borohydride solution is 3M sodium hydroxide (12 ml.). Liquids are decanted from the precipitated mercury. The organic layer is taken up in ether, washed with three portions of water and dried over sodium sulfate. Evaporation of the ether leaves 4.4 g. of ethyl 8-acetyl-12-hydroxy-12-methylheptadecanoate as a yellowish oil used in the next step without further purification; pmr (CDCl3) δ 0.88 (3H,t), 1.13 (3H,s, CH3COH), 1.25 (3H,t, CH3CH2OCO--), 2.12 (3H,s, CH3CO), 4.12 (2H,q).

Aufarbeitung

  1. customto give
  2. additiona suspension of a yellow solid
  3. waitAfter 6 hours
  4. customa cloudy solution results
  5. customLiquids are decanted from the precipitated mercury
  6. washwashed with three portions of water
  7. dry with materialdried over sodium sulfate
  8. customEvaporation of the ether
  9. customleaves 4.4 g
  10. customof ethyl 8-acetyl-12-hydroxy-12-methylheptadecanoate as a yellowish oil used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-6e553390d5e141868426a7068e310da1
Quelldatensatz
uspto-grants-1978_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04092356

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