1-Tetralone → 5-Nitro-3,4-dihydronaphthalen-1(2H)-one

HRID 1648237

Reaktionsgleichung

Reaktionsgleichung von HRID 1648237
[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.[N+:12]([O-])([O-:14])=[O:13].[K+]>S(=O)(=O)(O)O.CCOCC>[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=2[CH2:2]1

Komponenten

5

Edukt 2

HCID 107241-TetraloneHCID 24434Potassium Nitrate

Produkt 1

HCID 102619465-Nitro-3,4-dihydronaphthalen-1(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

10 ml (75 mmol) of α-tetralone was added dropwise to 7.6 g (75 mmol) of potassium nitrate dissolved in 75 ml of concentrated sulfuric acid (at -10° C). The resulting mixture was poured onto ice and the precipitate was suspended in ether. The precipitate (the 7 nitro isomer) was filtered off and the ether solution was evaporated. The residue was purified by column chromatography on silica gel. Yield: 4.7 g of the title compound, M.p. 94°-96° C.

Aufarbeitung

  1. additionThe resulting mixture was poured onto ice
  2. filtrationThe precipitate (the 7 nitro isomer) was filtered off
  3. customthe ether solution was evaporated
  4. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-eba699798e7e479dbfdbf80a05dae1a6
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05436250

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