Chlorosuccinimide → 1-(4-Chloro-1-hydroxy-naphthalen-2-YL)-ethanone

HRID 1192543

Reaktionsgleichung

Reaktionsgleichung von HRID 1192543
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].[Cl:15]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:15][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([OH:1])=[C:3]([C:12](=[O:14])[CH3:13])[CH:4]=1

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 697331'-Hydroxy-2'-acetonaphthone

Produkt 1

HCID 114814261-(4-Chloro-1-hydroxy-naphthalen-2-YL)-ethanoneAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred solution of 1-(1-hydroxy-2-naphthyl)ethanone (5.00 g, 26.8 mmol, from Aldrich) in acetic acid (100 mL) was added N-chlorosuccinimide (3.94 g, 29.5 mmol) and the resulting mixture heated at 100° C. for 18 hours. After allowing to be cooled to ambient temperature, the reaction mixture was concentrated in vacuo and then diluted with ethyl acetate. The precipitated solid was collected by filtration to afford the desired product (3.98 g, 67%). LCMS calculated for C12H10ClO2 (M+H)+: m/z=221.0; Found: 221.1.

Aufarbeitung

  1. temperatureto be cooled to ambient temperature
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additiondiluted with ethyl acetate
  4. filtrationThe precipitated solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-aa27fc8e005b4a8fb67e4c8e976c61fb
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680108B2

Verknüpfte Notizen

Wird geladen…