Chloranil → HCID 11460899, compound

HRID 749639Notes

Reaction equation

HRID 749639 reaction equation
[CH2:1]1[C:22]2[CH:5]([CH2:6][C:7]3[C:20]([CH:21]=2)=[CH:19][C:18]2[C:9](=[CH:10][C:11]4[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:8]=3)[CH2:4][CH2:3][CH2:2]1.[C:23]1(Cl)C(=O)C(Cl)=C(Cl)C(=O)[C:24]=1Cl.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH:13]1[CH:12]=[C:11]2[C:16]([CH:17]=[C:18]3[C:9](=[CH:10]2)[CH:8]2[C:7]4[C:20]([CH:19]3[CH:23]=[CH:24]2)=[CH:21][C:22]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=4)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8371ChloranilHCID 14798Sodium HydroxideHCID 131726974HCID 131726974, compound

Product 1

HCID 11460899HCID 11460899, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A stirred mixture of the hexahydropentacene (221.78 g, 0.720 mol), chloranil (362.6 g, 1.475 mol) and 4 L toluene is kept at reflux for 2½h. The mixture is cooled to about 50° C. and 350 mL 33% sodium hydroxide solution is gradually added. The organic layer is separarted, while the aquous layer is washed with toluene. The combined toluene layers are filtered over aluminium oxide and are rotary evaporated. The residue is stirred with a mixture of 500 mL toluene and heptane. Filtration and washing gives 188.0 g of the product (0.618 mol, 86%). 1H-NMR (CDCl3): δ 5.35 (dd, 2H), 7.05 (dd, 2H), 7.4 (m, 4H), 7.75 (m, 8H).

Workup

  1. temperatureat reflux for 2½h
  2. washis washed with toluene
  3. filtrationThe combined toluene layers are filtered over aluminium oxide
  4. filtrationFiltration
  5. washwashing

Sources & evidence

ORD record
ord-16a0a9c912ce4365a20e4085682014e9
Source dataset
uspto-grants-2008_07
Patent number
US07402707B2

Reaction notes

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