2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 11290387, compound

HRID 600129Notes

Reaction equation

HRID 600129 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[CH2:15]([C:18]1[C:27]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=2[C:21]([CH2:28][CH2:29][CH3:30])=[C:20]([C:31]([O:33][CH3:34])=[O:32])[C:19]=1[C:35]([O:37][CH3:38])=[O:36])[CH2:16][CH3:17]>C1C=CC=CC=1>[CH2:15]([C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH2:28][CH2:29][CH3:30])=[C:20]([C:31]([O:33][CH3:34])=[O:32])[C:19]=1[C:35]([O:37][CH3:38])=[O:36])[CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 15482398HCID 15482398, compound

Product 1

HCID 11290387HCID 11290387, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2,3-Dichloro-5,6-dicyanobenzoquinone (1.362 g, 6.0 mmols) was added to a solution of dimethyl 1,4-dipropyl-5,6,7,8-tetrahydronaphthalene-2,3-dicarboxylate (0.665 g, 2.0 mmols) in benzene (20 ml). The mixture was then refluxed for 24 hours. After filtration, the solvent in the mixture was removed in vacuum. By column chromatography (ethyl acetate/hexane, 1/20) using silica gel, 0.464 g of the title compound was obtained as colorless crystals. The GC yield was 87% and the isolation yield was 71%.

Workup

  1. temperatureThe mixture was then refluxed for 24 hours
  2. filtrationAfter filtration
  3. customthe solvent in the mixture was removed in vacuum

Sources & evidence

ORD record
ord-8e0b1d7d690d457a868e2f03522e4152
Source dataset
uspto-grants-2011_03
Patent number
US07901594B2

Reaction notes

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