Propionic Acid → 2-Ethylnaphthoquinone

HRID 1535017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1535017
[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.[C:13](O)(=O)[CH2:14]C.S1(CCCC1)(=O)=O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>C(#N)C.O.[N+]([O-])([O-])=O.[Ag+]>[CH2:13]([C:3]1[C:4](=[O:11])[C:5]2[C:10]([C:1](=[O:12])[CH:2]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:14]

Komponenten

8

Edukt 4

HCID 1032Propionic AcidHCID 85301,4-NaphthoquinoneHCID 31347SulfolaneHCID 62648Ammonium Persulfate

Produkt 1

HCID 949222-Ethylnaphthoquinone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24470Silver NitrateKatalysatorHCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 1,4-naphthoquinone (7.91 g), propanoic acid (3.70 g) and silver nitrate (1.53 g) in a mixture of acetonitrile (11.4 mL), sulfolane (34.1 mL) and water (79.5 mL) was heated at 60°-65° C. for 2 hours. A solution of ammonium persulfate (13.7 g) in water (25 mL) was then added dropwise. The mixture was cooled in ice water and extracted with ether. The organic layer was washed with saturated sodium bicarbonate, water and brine, then dried, filtered and evaporated. Chromatography over silica gel afforded 2-ethyl-1,4-naphthoquinone, m.p. 87°-88° C.

Aufarbeitung

  1. temperaturewas heated at 60°-65° C. for 2 hours
  2. extractionextracted with ether
  3. washThe organic layer was washed with saturated sodium bicarbonate, water and brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-234c580e3f164f1398d26ffa028cfc58
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05091558

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