2-Methoxynaphthalene → 3-Methoxyacenaphthoquinone

HRID 278963

Reaktionsgleichung

Reaktionsgleichung von HRID 278963
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[C:13](Cl)(=[O:17])[C:14](Cl)=[O:15].C(=O)=O.C(O)CO.[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5]3[C:4]=1[C:13](=[O:17])[C:14](=[O:15])[C:6]=3[CH:7]=[CH:8][CH:9]=2

Komponenten

6

Edukt 4

HCID 71192-MethoxynaphthaleneHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 86601574Dry ice ethyleneglycol

Produkt 1

HCID 22502643-MethoxyacenaphthoquinoneAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-methoxynaphthalene (5 g, 31.6 mmol) and oxalyl chloride (11 mL, 126 mmol) in 150 mL of dichloromethane was cooled to −15° C. (CO2/ethylene glycol) under nitrogen. Aluminum trichloride (10.5 g, 79 mmol) was added slowly over 30 minutes. After 3 hours, the mixture was poured onto 100 g of ice. The layers were separated, and the aqueous layer was washed with dichloromethane. The combined organic layers were washed with saturated sodium bicarbonate, water, brine and dried over magnesium sulfate. The solution was concentrated to afford 4.5 g of a solid. The solid was triturated with dichloromethane to give 1.24 g of the title compound as a solid, mp 218-220° C.;

Aufarbeitung

  1. customThe layers were separated
  2. washthe aqueous layer was washed with dichloromethane
  3. washThe combined organic layers were washed with saturated sodium bicarbonate, water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solution was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-05d9e3fec74d43c59653182e8ac3c7af
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362181B1

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