Acetaldehyde → 5-(2-Hydroxypropan-1-yl)-2-phenyl-1,3-dioxane

HRID 728485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 728485
Br[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.[Mg].[CH:16](=[O:18])[CH3:17].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[OH:18][CH:16]([CH3:17])[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

Komponenten

7

Edukt 4

HCID 177AcetaldehydeHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 148351015-Bromomethyl-2-phenyl-1,3-dioxane

Produkt 1

HCID 198842565-(2-Hydroxypropan-1-yl)-2-phenyl-1,3-dioxane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

To a solution of 19.39 g (75.4 mM) of 5-bromomethyl-2-phenyl-1,3-dioxane m2 in 200 ml of tetrahydrofuran is added 1.923 g (79.17 mM) of magnesium and the mixture is allowed to react for 7 hours under ultrasonic bibration. The mixture is cooled to -70° C. and 21.27 ml (377 mM) of acetaldehyde is added and then the mixture is stirred at 0° C. for 15 hours. The mixture is poured into an ice-cooled saturated aqueous ammonium chloride solution and 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. By eliminating the polar impurity by passing short column of silica gel, 11.353 g of the crude titled compound m3 is obtained which is used to the next reaction without further purification.

Aufarbeitung

  1. customto react for 7 hours under ultrasonic bibration
  2. washThe ethyl acetate layer is washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c843df144656408986309cb6590631f3
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05047540

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