2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 4-Oxocyclopent-2-en-1-yl acetate

HRID 2163163Notes

Reaction equation

HRID 2163163 reaction equation
[C:1]([O:4][CH:5]1[CH2:9][CH:8]([OH:10])[CH:7]=[CH:6]1)(=[O:3])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[C:1]([O:4][CH:5]1[CH2:9][C:8](=[O:10])[CH:7]=[CH:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 44282084-Hydroxycyclopent-2-en-1-yl acetate

Product 1

HCID 3431174-Oxocyclopent-2-en-1-yl acetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

144 milligrams of optically inactive 3-acetoxy-5-hydroxycyclopent-1-ene prepared as in Example 1 and 460 milligrams of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) were dissolved in 5 milliliters of dioxane, after which the resulting solution was heated with stirring for 48 hours at 60° C. The precipitate separating out after the reaction was separated by filtration, and the filtrate was concentrated under reduced pressure to obtain a crude product.

Workup

  1. temperatureafter which the resulting solution was heated
  2. customThe precipitate separating out after the reaction
  3. customwas separated by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3cecaeee6024494b85d3d4b2fca34825
Source dataset
uspto-grants-1979_01
Patent number
US04132726

Reaction notes

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