2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → (4-Methoxyphenyl)(2-phenylnaphthalen-1-yl)methanone

HRID 439328Notes

Reaction equation

HRID 439328 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][C:10]3[C:15]([C:16]=2[C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]([C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:26])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 12835030(4-Methoxyphenyl)(2-phenyl-3,4-dihydronaphthalen-1-yl)methanone

Product 1

HCID 22001239(4-Methoxyphenyl)(2-phenylnaphthalen-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title product was prepared as described in U.S. Pat. No. 4,230,862. To 30 ml of dioxane were added 3-phenyl-4-(4-methoxybenzoyl)-1,2-dihydronaphthalene (1.90 g, 5.58 mmol), prepared as described in Example 3, supra, and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (2.00 g, 8.81 mmol). The resulting mixture was heated to reflux and refluxed for twelve hours under a nitrogen atmosphere. The mixture was then cooled and evaporated to dryness. The residue was partitioned between ether and water. The organic fraction was washed 5N sodium hydroxide (5×20 ml), followed by a wash with brine. The mixture was then dried over magnesium sulfate and evaporated to give 1.9 grams of substantially pure 1-(4-methoxybenzoyl)-2-phenylnaphthalene.

Workup

  1. customprepared
  2. temperatureThe resulting mixture was heated
  3. temperatureto reflux
  4. temperaturerefluxed for twelve hours under a nitrogen atmosphere
  5. temperatureThe mixture was then cooled
  6. customevaporated to dryness
  7. customThe residue was partitioned between ether and water
  8. washThe organic fraction was washed 5N sodium hydroxide (5×20 ml)
  9. washa wash with brine
  10. dry with materialThe mixture was then dried over magnesium sulfate
  11. customevaporated

Sources & evidence

ORD record
ord-43aab8513733468dacf91924cd098d84
Source dataset
uspto-grants-1996_05
Patent number
US05514675

Reaction notes

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