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

HRID 2285626Notes

Reaction equation

HRID 2285626 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

To 30 ml. of dioxane were added 1.90 grams (5.58 mmoles) of 3-phenyl-4-(4-methoxybenzoyl)-1,2-dihydronaphthalene (prepared as in Example 3) and 2.00 grams (8.81 mmoles) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The resulting mixture was heated at reflux for twelve hours in a nitrogen atmosphere. The mixture then was cooled and evaporated to dryness. Water and ether were added to the residue. The ether layer was separated and washed 5 times with 20 ml. portions of 5 N sodium hydroxide and then with aqueous sodium chloride. The mixture then was dried over magnesium sulfate and evaporated to give 1.9 grams of substantially pure 1-(4-methoxybenzoyl)-2-phenylnaphthalene as a green oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for twelve hours in a nitrogen atmosphere
  3. temperatureThe mixture then was cooled
  4. customevaporated to dryness
  5. additionWater and ether were added to the residue
  6. customThe ether layer was separated
  7. washwashed 5 times with 20 ml
  8. dry with materialThe mixture then was dried over magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-3d3d9bb799714dc29bff68c34ad7ea77
Source dataset
uspto-grants-1982_04
Patent number
US04323707

Reaction notes

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