Acetic Anhydride → 2-Acetyl-1H-indene-1,3(2H)-dione

HRID 1884554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1884554
C(N(CC)CC)C.[C:8](OC(=O)C)(=[O:10])[CH3:9].[C:15]1(=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[CH2:16]1>CN(C)C1C=CN=CC=1.ClCCCl>[C:8]([CH:16]1[C:15](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=[O:24])(=[O:10])[CH3:9]

Komponenten

6

Edukt 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 118151,3-Indandione

Produkt 1

HCID 708102-Acetyl-1H-indene-1,3(2H)-dioneAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 111,2-DichloroethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A mixture of 4-dimethylaminopyridine (664 mg, 5.44 mmol), triethylamine (7.6 ml 54.56 mmol), acetic anhydride (6.2 ml, 65.48 mmol in dry 1,2-dichloroethane (60,ml) was stirred at −20° C. and a solution of 1,3-indanedione (7.96 g, 54.56 mmol) in 1,2-dichloroethane was added dropwise in 1.5 h. The reaction mixture was stirred for 30 min, then washed with 10% hydrochloric acid (80 ml) and twice with water (80 ml). The organic phase was dried over MgSO4 and evaporated. The residue was crystallized from methyl-tert-butylether (50 ml) to give 2-acetyl-1,3-indanedione 38(6.5 g 63%). Rf 0.27 (hexane-ethylacetate-acetic acid 20-5-0.5) MS C11H8O3 m/z (%) 189 [M+H]+ (100), 166 (72), 104 (20).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 30 min
  2. washwashed with 10% hydrochloric acid (80 ml) and twice with water (80 ml)
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated
  5. customThe residue was crystallized from methyl-tert-butylether (50 ml)

Quellen und Nachweise

ORD-Eintrag
ord-6d55cd5fd8d24b479096b65c6303e962
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06765089B1

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