Thionyl Chloride → Anthraquinone-2-carbonyl Chloride

HRID 1636199

Reaktionsgleichung

Reaktionsgleichung von HRID 1636199
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][C:2]=1[C:17]([OH:19])=O.S(Cl)([Cl:22])=O>ClCCl>[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][C:2]=1[C:17]([Cl:22])=[O:19]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 670302-Anthraquinonecarboxylic acid

Produkt 1

HCID 15025286Anthraquinone-2-carbonyl Chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Anthraquinone-2-carboxylic acid (2.52 g, 10 mmol) was suspended in dichloro methane (100 ml). Thionyl chloride (50 ml) was added and the mixture heated to reflux in a nitrogen atmosphere for several hours giving a clear yellow solution. Dichloro methane and excess thionyl chloride was removed in vacuo giving a yellow solid. The solid was filtered off, washed several times with petroleum ether and dried in vacuo. Yield 2.69 g (99% from anthraquinone-2-carboxylic acid); MP: 143-144.5° C.; TLC (analyzed as the methyl ester: a small sample of the acid chloride was dissolved in dry methanol and analyzed immediately using ethyl acetate as eluent); Rf =0.68. MS (FAB+): 307.1 (MH+).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureto reflux in a nitrogen atmosphere for several hours
  3. customgiving a clear yellow solution
  4. customDichloro methane and excess thionyl chloride was removed in vacuo
  5. customgiving a yellow solid
  6. filtrationThe solid was filtered off
  7. washwashed several times with petroleum ether
  8. customdried in vacuo
  9. dissolutiona small sample of the acid chloride was dissolved in dry methanol

Quellen und Nachweise

ORD-Eintrag
ord-f33fec283bf24b3ba13503f2623c2424
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06033784

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