Chloranil → HCID 10305781, compound

HRID 600128Notes

Reaction equation

HRID 600128 reaction equation
C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl.[CH2:13]([C:16]1[C:37]2[CH2:36][C:35]3[C:22](=[C:23]([CH2:53][CH2:54][CH3:55])[C:24]4[C:33]([C:34]=3[CH2:38][CH2:39][CH3:40])=[CH:32][C:31]3[C:26](=[C:27]([CH2:50][CH2:51][CH3:52])[C:28]([CH2:47][CH2:48][CH3:49])=[C:29]([CH2:44][CH2:45][CH3:46])[C:30]=3[CH2:41][CH2:42][CH3:43])[CH:25]=4)[CH2:21][C:20]=2[C:19]([CH2:56][CH2:57][CH3:58])=[C:18]([C:59]([O:61][CH3:62])=[O:60])[C:17]=1[C:63]([O:65][CH3:66])=[O:64])[CH2:14][CH3:15]>C1C=CC=CC=1>[CH2:13]([C:16]1[C:37]2[C:20](=[CH:21][C:22]3[C:35]([CH:36]=2)=[C:34]([CH2:38][CH2:39][CH3:40])[C:33]2[C:24](=[CH:25][C:26]4[C:31]([CH:32]=2)=[C:30]([CH2:41][CH2:42][CH3:43])[C:29]([CH2:44][CH2:45][CH3:46])=[C:28]([CH2:47][CH2:48][CH3:49])[C:27]=4[CH2:50][CH2:51][CH3:52])[C:23]=3[CH2:53][CH2:54][CH3:55])[C:19]([CH2:56][CH2:57][CH3:58])=[C:18]([C:59]([O:61][CH3:62])=[O:60])[C:17]=1[C:63]([O:65][CH3:66])=[O:64])[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 8371ChloranilHCID 15482434HCID 15482434, compound

Product 1

HCID 10305781HCID 10305781, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Chloranil (0.054 g, 0.22 mmol) was added to a solution of dimethyl 5,14-dihydro-1,4,6,8,9,10,11,13-octapropylpentacene-2,3-dicarboxylate (0.147 g, 0.2 mmol) obtained in REFERENCE EXAMPLE 6 in benzene (5 ml). The mixture was then refluxed for 24 hours. After concentration, chloroform was added to the residue followed by filtration. After concentration, the concentrate was recrystallized from benzene to give 0.048 g of the title compound as a blue solid. The isolation yield was 33%.

Workup

  1. temperatureThe mixture was then refluxed for 24 hours
  2. concentrationAfter concentration, chloroform
  3. additionwas added to the residue
  4. filtrationfollowed by filtration
  5. concentrationAfter concentration
  6. customthe concentrate was recrystallized from benzene

Sources & evidence

ORD record
ord-4284ea5a60ac4208b15de76c9a27d03f
Source dataset
uspto-grants-2011_03
Patent number
US07901594B2

Reaction notes

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