Acetic Acid → 6-Methoxy-7-nitro-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1893558Notes

Reaction equation

HRID 1893558 reaction equation
[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.[N+:14]([O-])([OH:16])=[O:15].C(O)(=O)C>C(OC(=O)C)(=O)C.CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:14]([O-:16])=[O:15])[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 141126-Methoxy-alpha-tetralone

Product 1

HCID 130673386-Methoxy-7-nitro-1,2,3,4-tetrahydronaphthalen-1-oneYield 24%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7918Acetic AnhydrideSolvent

Procedure

6-Methoxy-1-tetralone (12.0 g, 68.1 mmol) was dissolved in acetic anhydride (60 ml), a fuming nitric acid (4.8 ml)-acetic acid (4.2 ml) mixed solvent was slowly added dropwise under ice-cooling with stirring, and thereafter the mixture was stirred at the same temperature for 2 hr. The reaction mixture was diluted with ether, and the precipitated solid was collected by filtration and dried under reduced pressure. The obtained solid was recrystallized from benzene (100 ml), and the precipitated solid was filtered, dried under reduced pressure to give the title compound (3.62 g, yield 24%) as a colorless solid.

Workup

  1. additionwas slowly added dropwise under ice-
  2. temperaturecooling
  3. stirringthe mixture was stirred at the same temperature for 2 hr
  4. filtrationthe precipitated solid was collected by filtration
  5. customdried under reduced pressure
  6. customThe obtained solid was recrystallized from benzene (100 ml)
  7. filtrationthe precipitated solid was filtered
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-63adfeb991a24dfe8923cf883f3430a3
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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