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

HRID 891172

Reaction equation

HRID 891172 reaction equation
C1C2C(=CC=CC=2)CCC1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19](=[O:23])[CH2:18][CH2:17][CH2:16]2.S(=O)(=O)(O)O.[N+:29]([O-:32])([OH:31])=[O:30]>CC(C)=O>[CH3:11][O:12][C:13]1[C:14]([N+:29]([O-:31])=[O:30])=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19](=[O:23])[CH2:18][CH2:17][CH2:16]2.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[N+:29]([O-:32])=[O:30])[C:19](=[O:23])[CH2:18][CH2:17][CH2:16]2

Participants

7

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 8404TetralinHCID 141126-Methoxy-alpha-tetralone

Product 2

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

A procedure for the synthesis of mono-amino substituted tetralone from tetrahydronaphthalene is illustrated with an exemplary synthetic route in FIG. 4. To an ice-cold, stirred solution of 6-methoxy-1-tetralone (20, 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 (21, 7.74 g, 0.035 mol) and 6-methoxy-7-nitro-1-tetralone (22, 6.63 g, 0.030 mol) were obtained after purification by column chromatography:

Workup

  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

Sources & evidence

ORD record
ord-ada52aa9e60c4c81b5bfdb74b0437189
Source dataset
uspto-grants-2006_02
Patent number
US07001926B2

Linked notes

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