Acetone → 4-[(4-Bromophenoxy)methyl]-2,2,4-trimethyl-1,3-dioxolane

HRID 1909091

Reaktionsgleichung

Reaktionsgleichung von HRID 1909091
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([CH3:12])([OH:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.[CH3:15][C:16]([CH3:18])=O.O1CCCC1.C(=O)([O-])[O-].[Na+].[Na+]>O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]2([CH3:12])[CH2:9][O:10][C:16]([CH3:18])([CH3:15])[O:11]2)=[CH:13][CH:14]=1

Komponenten

7

Edukt 4

HCID 180Acetone2×HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 71059322HCID 71059322, Verbindung

Produkt 1

HCID 710593314-[(4-Bromophenoxy)methyl]-2,2,4-trimethyl-1,3-dioxolaneAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-(4-Bromophenoxy)-2-methylpropane-1,2-diol (261 mg, 1.00 mmol), acetone (77 mg, 1.3 mmol), tetrahydrofuran (5 mL), and a boron trifluoride diethyl ether complex (3 drops) were mixed. The mixture was stirred at room temperature for 67 hours, and acetone (102 mg, 1.76 mmol) was added thereto, followed by stirring for 2 hours. Sodium carbonate, ethyl acetate, and water were added to the reaction mixture to conduct extraction. The organic layer was washed with a saline solution twice. A residue was obtained by concentrating the organic layer under reduced pressure, and the residue was subjected to chromatography refining (methylene chloride) using silica gel, obtaining 121 mg of the objective compound (yield: 40%).

Aufarbeitung

  1. stirringby stirring for 2 hours
  2. extractionextraction
  3. washThe organic layer was washed with a saline solution twice
  4. customA residue was obtained
  5. concentrationby concentrating the organic layer under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-771e027b372243a5a31bf786fb682a8a
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598358B2

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