Nitric Acid → 6-Methoxy-5-nitro-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1357870

Reaktionsgleichung

Reaktionsgleichung von HRID 1357870
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.S(=O)(=O)(O)O.[N+:19]([O-:22])([OH:21])=[O:20]>CC(C)=O>[CH3:1][O:2][C:3]1[C:4]([N+:19]([O-:21])=[O:20])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:19]([O-:22])=[O:20])[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2

Komponenten

6

Edukt 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 141126-Methoxy-alpha-tetralone

Produkt 2

HCID 130673376-Methoxy-5-nitro-1,2,3,4-tetrahydronaphthalen-1-oneHCID 13067338HCID 13067338, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To an ice-cold, stirred sloution of 6-methoxy-1-tetralone (17.6 g, 0.10 mol) in acetone (30 mL) was added dropwise a mixture of sulfuric acid (18 mL, 96.0%) and nitric acid (15 mL, 68.0-70.0%). After the addition was complete, the reaction was stirred at 0° C. for 6 hours, and TLC was employed to monitor the reaction progress. The reaction mixture was poured into ice-water, and the mixture was partitioned between CH2Cl2 (3*200 mL) and water (200 mL). The organic layer was washed by saturated NaHCO3 solution and water (200 mL each), dried over anhydrous sodium sulfate, and, after filtration, the organic layer was concentrated in vacuo to provide a yellow oil. 6-Methoxy-5-nitro-1-tetralone (7.74 g, 0.035 mol) and 6-methoxy-7-nitro-1-tetralone (6.63 g, 0.030 mol) was obtained after purification by column chromatography.

Aufarbeitung

  1. additionwas added dropwise
  2. additionAfter the addition
  3. customthe mixture was partitioned between CH2Cl2 (3*200 mL) and water (200 mL)
  4. washThe organic layer was washed by saturated NaHCO3 solution and water (200 mL each)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationafter filtration
  7. concentrationthe organic layer was concentrated in vacuo
  8. customto provide a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-08a49c84b1564e4e88040a767e1f03c2
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593374B2

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