6-Chloronaphthalen-1-ol → 6-Chloronaphthalene-1,2-dione

HRID 1665266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1665266
C1(C([O:9]C(C2C=CC=CC=2)=[Se])=[Se])C=CC=CC=1.[Cl:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25]([OH:29])=[CH:24][CH:23]=[CH:22]2>O1CCCC1>[Cl:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25](=[O:29])[C:24](=[O:9])[CH:23]=[CH:22]2

Komponenten

4

Edukt 2

HCID 132157076-Chloronaphthalen-1-olHCID 86588323O-(benzenecarbonoselenoyl) benzenecarboselenoate

Produkt 1

HCID 203740386-Chloronaphthalene-1,2-dioneAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of benzeneselenic anhydride (3.18 g, 8.8 mmol) in tetrahydrofuran (30 ml), which had been heated to 70° C. was added a solution of 6-chloro-1-naphthol (1.5 g, 8.4 mmol) in tetrahydrofuran (5 ml). The reaction was maintained at 70° C. for 15 minutes. The mixture was then concentrated under reduced pressure. The residue was suspended in hexanes (100 ml) and filtered. This was repeated 5 times. The residue was dissolved in dichloromethane (100 ml), filtered and concentrated under reduced pressure to afford the product as an orange solid (1.33 g, 82%); 400 MHz 1H NMR (CDCl3) δ: 8.06 (d, J=8.4 Hz, 1H), 7.49 (dd, J=2 and 8.4 Hz, 1H), 7.41-7.38 (m, 2H), 6.50 (d, J=10 Hz, 1H).

Aufarbeitung

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. filtrationfiltered
  3. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0deb652d776842829d3c78371d60e6d1
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039503B2

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