Ethyl vinyl ether → 6-(1-Ethoxy ethoxy)-2-naphthaldehyde

HRID 734166

Reaktionsgleichung

Reaktionsgleichung von HRID 734166
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]=[O:13])[CH:6]=[CH:5]2.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.[CH:31]([O:33][CH2:34][CH3:35])=[CH2:32]>C(OCC)=C.C(OCC)(=O)C>[CH2:31]([O:33][CH:34]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]=[O:13])[CH:6]=[CH:5]2)[CH3:35])[CH3:32]

Komponenten

6

Edukt 3

HCID 8023Ethyl vinyl ether2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 27641106-Hydroxy-2-naphthaldehyde

Produkt 1

HCID 231357596-(1-Ethoxy ethoxy)-2-naphthaldehydeAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8023Ethyl vinyl etherKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a 500 mL three neck flask, equipped with a magnetic stirrer, an addition funnel, and a reflux condenser, were charged 25 g of HNAL (0.1462 mol) and 300 mL of ethyl acetate. 6-Hydroxy-2-naphthaldeyde was not completely soluble even after 3 h stirring at room temperature. To this was added 3.30 g of PPTS (0.0131 mol) and the solution mixture was heated to 70° C. At this temperature, 21 g of ethyl vinyl ether (0.2912 mol) was added dropwise and the reaction mixture became homogeneous upon addition of a few drops of ethyl vinyl ether. After completion of ethyl vinyl ether addition, the reaction temperature was lowered to room temperature and the reaction mixture was stirred overnight. The crude product was purified by column chromatography (silica gel, CH2Cl2) to yield 26 g of pure 6-(1-ethoxy ethoxy)-2-naphthaldehyde (yield: 73%).

Aufarbeitung

  1. temperaturethe solution mixture was heated to 70° C
  2. customwas lowered to room temperature
  3. stirringthe reaction mixture was stirred overnight
  4. customThe crude product was purified by column chromatography (silica gel, CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-d081de253417462eb0dd24569da1e53f
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592125B2

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