2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-Formyl-6-phenylphenol

HRID 1032890Notes

Reaction equation

HRID 1032890 reaction equation
[OH:1][C:2]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.CCCCCC.C(OCC)(=O)C>O1CCOCC1>[C:10]1([C:9]2[CH:8]=[CH:7][CH:6]=[C:3]([CH:4]=[O:5])[C:2]=2[OH:1])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8058HexaneHCID 8857Ethyl AcetateHCID 125452552-Hydroxy[1,1′-biphenyl]-3-methanol

Product 1

HCID 107031002-Formyl-6-phenylphenolYield 82.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-hydroxy-3-phenylbenzyl alcohol (2.00 g, 10 mmol) in dioxane (100 ml) was added 2,3- dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (2.50 g, 11 ml) at room temperature. The reaction mixture immediately became a black solution. This solution was stirred at room temperature for 2 hours and further heated under refluxing for 2 hours. The solvent was removed under reduced pressure to obtain deep-black oily residue. This was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 1.63 g (82%) of 3-phenylsalicylaldehyde as a light yellow oil.

Workup

  1. temperaturefurther heated
  2. temperatureunder refluxing for 2 hours
  3. customThe solvent was removed under reduced pressure
  4. customto obtain deep-black oily residue

Sources & evidence

ORD record
ord-0b8ba87e504b40eb844365b20925630a
Source dataset
uspto-grants-1994_05
Patent number
US05308820

Reaction notes

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