Diethyl Oxalate → 2-Ethoxalylacenaphthen-1-one

HRID 1722057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1722057
[C:1]1(=[O:13])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1.[C:14](OCC)(=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].[O-]CC.[Na+]>C(O)C>[C:14]([CH:2]1[C:3]2[C:12]3[C:7]([CH:6]=[CH:5][CH:4]=2)=[CH:8][CH:9]=[CH:10][C:11]=3[C:1]1=[O:13])([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:20]

Komponenten

5

Edukt 3

HCID 7268Diethyl OxalateHCID 752291-AcenaphthenoneHCID 2723922Sodium ethoxide

Produkt 1

HCID 200301742-Ethoxalylacenaphthen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Acenaphthen-1-one (JACS, 62, 432, 1940) (4.1 g) is reacted with diethyl oxalate (4.2 g) in anhydrous ethanol (280 ml) containing sodium ethoxide (from 0.66 g of sodium) at room temperature for 2 hours. The precipitate is filtered and washed with hexane, then is dissolved in water. The aqueous solution is acidified to pH 4 with citric acid and the precipitate is filtered and washed with water. Crystallization from chloroform-hexane gives 2-ethoxalylacenaphthen-1-one, m.p. 101°-103° C. (5.1 g), which is reacted with methylhydrazide (1.3 g) in acetic acid (110 ml) at 60° C. for 4 hours. After cooling the reaction mixture is diluted with ice water and extracted with ethyl acetate.

Aufarbeitung

  1. filtrationThe precipitate is filtered
  2. washwashed with hexane
  3. dissolutionis dissolved in water
  4. filtrationthe precipitate is filtered
  5. washwashed with water
  6. customCrystallization from chloroform-hexane

Quellen und Nachweise

ORD-Eintrag
ord-38379174472e4722816505b781d37481
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04853405

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