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

HRID 1096823Notes

Reaction equation

HRID 1096823 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[OH:11].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Cl:10])[C:3]=1[OH:11])[CH:8]=[O:9]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 176409Benzenemethanol, 3,5-dichloro-4-hydroxy-

Product 1

HCID 168393,5-Dichloro-4-hydroxybenzaldehydeYield 22%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CH2Cl2, and the mixture was filtered. The filtrate was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization from EtOAc yielded the title compound (0.77 g, 22%). LC-MS: tR=0.82 min.

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionThe residue was diluted with CH2Cl2
  3. filtrationthe mixture was filtered
  4. dry with materialThe filtrate was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customCrystallization from EtOAc

Sources & evidence

ORD record
ord-771dbcb00c9447bc92e7895d8fa37ff7
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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