Acetic Anhydride → HCID 23356093, Verbindung

HRID 233627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 233627
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6](O)[C:5]2[C:10]([C:12]3[C:17]([C:18](=[O:19])[C:4]=2[C:3]=1O)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:11].[C:21](OC(=O)C)(=[O:23])[CH3:22].CN(C1C=CC=CN=1)C.[C:37](OCC)(=[O:39])[CH3:38]>C(Cl)Cl>[C:21]([C:6]1[C:5]2[C:10](=[O:11])[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18](=[O:19])[C:4]=2[C:3]([C:37](=[O:39])[CH3:38])=[C:2]([CH3:1])[C:7]=1[CH3:8])(=[O:23])[CH3:22]

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 218852-DimethylaminopyridineHCID 1005741,4-Dihydroxy-2,3-dimethyl-9,10-anthraquinone

Produkt 1

HCID 23356093HCID 23356093, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred suspension of 2,3-dimethylquinizarin (5.00 g, 18.637 mmol) in dry CH2Cl2 (250 ml) was added acetic anhydride (40 ml) pyridine (40 ml) and dimethylaminopyridine (DMAP, 1.7 g) at room temperature under argon. After two hours, the reaction mixture was poured into a mixture of ethyl acetate and ice (1:1, 800 ml), extracted with CH2Cl2, and the combined organic layers were dryed over MgSO4. Flash chromatography with toluene and ethylacetate; (95.5%) gave 2.517 g of pure compound (38% yield). (MP: 222°-224° C.). 1H NMR (CDCl3) δ:2.27 (s, 6H, CH3, 2.53 (s, 6H, COCH3), 7.72 (m, 2H, ArH), 8.15 (m, 2H, ArH).

Aufarbeitung

  1. extractionextracted with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-fa0b748bb55549fd8c951abda2e5d3b4
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05593970

Notizen zur Reaktion

Wird geladen…