Hydrochloric Acid → 3-Methyl-1,3-octandiol

HRID 1888305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1888305
[OH:1][C:2]([CH3:14])([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:3][C:4](OCC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.Cl>O1CCCC1>[CH3:14][C:2]([OH:1])([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:3][CH2:4][OH:5]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 3020787Ethyl 3-hydroxy-3-methyloctanoateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 231481413-Methyl-1,3-octandiolAusbeute 93,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of the compound 37 (13.86 g) in tetrahydrofuran (100 mL) was added dropwise to a suspension of lithium aluminum hydride (3.9 g) in tetrahydrofuran (100 mL) at 0° C. After 35 minutes, to the reaction solution was added ethyl acetate at 0° C. until foam was lost and 5N hydrochloric acid (20 mL) was added dropwise thereto. The solution temperature was risen to room temperature and the solution was stirred overnight. The reaction solution was dried over anhydrous magnesium sulfate, filtrated through Celite (Brand name) and concentrated. The obtained residue was purified by flush column chromatography (n-hexane:ethyl acetate=1:1), to give the title compound (10.31 g) having the following physical data.

Aufarbeitung

  1. customwas risen to room temperature
  2. dry with materialThe reaction solution was dried over anhydrous magnesium sulfate
  3. filtrationfiltrated through Celite (Brand name)
  4. concentrationconcentrated
  5. customThe obtained residue was purified
  6. customby flush column chromatography (n-hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-33b382722c24459fb47d6c4d53d9b19a
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501793B2

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