Acetic Acid → 1,5 dichloro-9(10H)-anthracenone

HRID 841104

Reaktionsgleichung

Reaktionsgleichung von HRID 841104
[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([Cl:17])[CH:10]=[CH:11][CH:12]=3)[C:7](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl[Sn]Cl.Cl.C(O)(=O)C>CCOCC>[Cl:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([Cl:17])[CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 67111,5-DichloroanthraquinoneHCID 24479Stannous Chloride

Produkt 1

HCID 4171641,5 dichloro-9(10H)-anthracenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

1,5-dichloroanthraquinone (1) was reduced with SnCl2 in boiling HCl and acetic acid with ether cleavage to give the corresponding 1,5 dichloro-9(10H)-anthracenone (II). To a solution of 1,5-dichloro-9(10H)anthracenone (1 mmol) and 0. 1 mL of pyridine in dry CH2Cl2 (20 mL) was added dropwise a solution of an appropriate acyl chloride (3 mmol) in dry CH2Cl2 (10 mL) under N2. The reaction mixture was stirred at room temperature or refluxed for several hours. The solvent was removed and the residue purified by recrystallization and chromatography. This procedure was used to synthesize each of the compounds in Table 1.

Quellen und Nachweise

ORD-Eintrag
ord-3384011617814b988879b6bd04080bbb
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06369246B2

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