Hydrochloric Acid → Ethyl 3-(naphthalen-8-yl)-3-oxopropanoate

HRID 1610400

Reaktionsgleichung

Reaktionsgleichung von HRID 1610400
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(O)C.[H-].[Na+].Cl.[C:20](=O)([O:24]CC)[O:21][CH2:22][CH3:23]>O>[C:4]1([C:1]([CH2:2][C:20]([O:21][CH2:22][CH3:23])=[O:24])=[O:3])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7766Diethyl CarbonateHCID 136631-AcetylnaphthaleneHCID 24758Sodium hydride

Produkt 1

HCID 2760157Ethyl 3-(naphthalen-8-yl)-3-oxopropanoateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 1′-acetonaphthone (28.29 g, 0.1662 mmol) and ethanol (0.5 ml) in diethyl carbonate (200 ml) was added sodium hydride (13.3 g, 60% in oil, 0.332 mol) by small portions and the mixture was stirred at 80° C. for 1.5 hrs. The reaction solution was poured into water, acidified with dilute hydrochloric acid and extracted twice with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1-6:1) to give ethyl (1-naphthoyl)acetate (38.14 g, 95%) as a yellow liquid.

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1-6:1)

Quellen und Nachweise

ORD-Eintrag
ord-d4367cef70914e0fb9caebac28dcb0ac
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06982348B2

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