2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1,2,3,4,6,11-Hexapropylnaphthacene

HRID 600143

Reaction equation

HRID 600143 reaction equation
[CH2:1]([C:4]1[C:21]2[CH2:20][C:19]3[C:10](=[C:11]([CH2:25][CH2:26][CH3:27])[C:12]4[C:17]([C:18]=3[CH2:22][CH2:23][CH3:24])=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:9][C:8]=2[C:7]([CH2:28][CH2:29][CH3:30])=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[CH2:34][CH2:35][CH3:36])[CH2:2][CH3:3].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH2:28]([C:7]1[C:8]2[C:21](=[CH:20][C:19]3[C:10]([CH:9]=2)=[C:11]([CH2:25][CH2:26][CH3:27])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]=3[CH2:22][CH2:23][CH3:24])[C:4]([CH2:1][CH2:2][CH3:3])=[C:5]([CH2:34][CH2:35][CH3:36])[C:6]=1[CH2:31][CH2:32][CH3:33])[CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 178395091,2,3,4,6,11-Hexapropyl-5,12-dihydrotetracene

Product 1

HCID 230670861,2,3,4,6,11-HexapropylnaphthaceneYield 36%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5,12-Dihydro-1,2,3,4,6,11-hexapropylnaphthacene (0.503 g, 1.04 mmol), 2,3-dichloro-5,6-dicyanobenzoquinone (0.260 g, 1.14 mmol) and 1,4-dioxane (3 ml) were charged in a reactor. The mixture was refluxed for 24 hours. After cooling, the precipitates were removed by filtration. The solvent in the mixture was removed in vacuum followed by recrystallization from chloroform/methanol. The orange red title compound (0.112 g) was obtained. The NMR yield was 36% and the isolation yield was 22%.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. temperatureAfter cooling
  3. customthe precipitates were removed by filtration
  4. customThe solvent in the mixture was removed in vacuum
  5. customfollowed by recrystallization from chloroform/methanol

Sources & evidence

ORD record
ord-5b21c6cd30d14b6eabb6f23e4e444a11
Source dataset
uspto-grants-2011_03
Patent number
US07901594B2

Linked notes

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