Ethyl Acetate → 3-methyl-6-nitro-2,3-dihydro-1H-inden-1-one

HRID 593264

Reaktionsgleichung

Reaktionsgleichung von HRID 593264
[N+:1]([O-:4])([O-])=[O:2].[K+].[CH3:6][CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[CH2:8]1.C(OCC)(=O)C>S(=O)(=O)(O)O>[CH3:6][CH:7]1[C:15]2[C:10](=[CH:11][C:12]([N+:1]([O-:4])=[O:2])=[CH:13][CH:14]=2)[C:9](=[O:16])[CH2:8]1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 24434Potassium NitrateHCID 2595603-Methyl-indan-1-one

Produkt 1

HCID 6007023-methyl-6-nitro-2,3-dihydro-1H-inden-1-oneAusbeute 69,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

As presented in the following reaction formula, a solution of potassium nitrate (KNO2; 6.2 g, 0.06 mol) in sulfuric acid (30 mL) was added dropwise at 0° C. to a mixture of 3-methyl-2,3-dihydro-1H-inden-1-one (9.0 g, 0.06 mol) in sulfuric acid ic (H2SO4; 40 mL). Then, the mixture was stirred at 0° C. until the completion of reaction. The mixture obtained after the reaction was added to ice water and filtered. The cake was washed with water and purified by silica gel (100 g) column chromatography (product of Merck Co., Ltd.) using an eluent of pentane (PE):ethyl acetate (10:1 (by volume)) to give 3-methyl-6-nitro-2,3-dihydro-1-H-inden-1-one (8 g, yield: 69%) as a yellow solid.

Aufarbeitung

  1. customThe mixture obtained after the reaction
  2. filtrationfiltered
  3. washThe cake was washed with water
  4. custompurified by silica gel (100 g) column chromatography (product of Merck Co., Ltd.)

Quellen und Nachweise

ORD-Eintrag
ord-381802b282e545cfbb890127ce167718
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242928B2

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