Ethyl Acetate → 5-Hexadecyloxymethyl-2-phenyl-1,3-dioxane

HRID 728494

Reaktionsgleichung

Reaktionsgleichung von HRID 728494
[OH:1][CH2:2][CH:3]1[CH2:8][O:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5][CH2:4]1.[H-].[Na+].CS(O[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])(=O)=O.C(OCC)(=O)C>C1C=CC=CC=1>[CH2:37]([O:1][CH2:2][CH:3]1[CH2:4][O:5][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:7][CH2:8]1)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:22]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 519810Hexadecyl methanesulfonateHCID 10679342(2-Phenyl-1,3-dioxan-5-yl)methanol

Produkt 1

HCID 198842025-Hexadecyloxymethyl-2-phenyl-1,3-dioxaneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A suspension of 7.769 g (40 mM) of 5-hydroxymethyl-2-phenyl-1,3-dioxane n1 and 2.08 g (52 mM) of 60% sodium hydride in oil in 150 ml of anhydrous benzene is heated at 50° C. for 1 hour then a solution of 17.28 g (54 mM) of n-hexadecyl methanesulfonate in 50 ml of anhydrous benzene is added. The reaction mixture is heated under refluxing for 7 hours. The product is isolated by ethyl acetate extraction. The ethyl acetate layer is washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated. Crystallization of the residue from n-pentane-methanol affords 16.203 g (97% yield) of the titled compound n2.

Aufarbeitung

  1. temperatureThe reaction mixture is heated
  2. temperatureunder refluxing for 7 hours
  3. washThe ethyl acetate layer is washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customCrystallization of the residue from n-pentane-methanol

Quellen und Nachweise

ORD-Eintrag
ord-77066b4b4e9243eaa30cff8652522946
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05047540

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