Hydrogen iodide → HCID 15508788, compound

HRID 2296594Notes

Reaction equation

HRID 2296594 reaction equation
[C:1]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1(O)[C:28]2[C:19](=[CH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:18]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)(O)[C:17]2[C:8]1=[CH:9][C:10]1[C:15]([CH:16]=2)=[C:14]2[CH:42]=[CH:43][CH:44]=[CH:45][C:13]2=[CH:12][CH:11]=1.I.C(=O)([O-])O.[Na+]>C(OC(C)C)(C)C.ClCCl>[C:1]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]2[C:17]([C:18]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[C:19]3[C:28]=1[CH:27]=[C:26]1[C:21]([CH:22]=[CH:23][CH:24]=[CH:25]1)=[CH:20]3)=[CH:16][C:15]1[C:10](=[CH:11][CH:12]=[C:13]3[CH:45]=[CH:44][CH:43]=[CH:42][C:14]3=1)[CH:9]=2

Participants

6

Reactant 3

HCID 24841Hydrogen iodideHCID 516892Sodium BicarbonateHCID 15508787HCID 15508787, compound

Product 1

HCID 15508788HCID 15508788, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7914Diisopropyl EtherSolvent

Procedure

In 150 ml of isopropyl ether and 75 ml of dichloromethane, 1.5 g (2.3 mmole) of 8,15-bis(p-biphenylyl)-8,15-dihydro-8,15-dihydroxybenzo[a]-pentacene was suspended. To the obtained suspension, 40 ml of a 57% aqueous solution of hydrogen iodide was added under the refluxing condition and the obtained mixture was stirred for 5 minutes. After the reaction was completed, the reaction solution was added to 500 ml of a saturated aqueous solution of sodium hydrogencarbonate and the obtained mixture was stirred for 10 minutes. The formed precipitates were separated by filtration and washed once with ion-exchanged water, once with a saturated aqueous solution of sodium disulfite and then three times with ion-exchanged water. The washed precipitates were dried under heating at a reduced pressure and 0.84 g (the yield: 51%) of a light purple solid of 8,15-bis(p-biphenylyl)benzo[a]pentacene was obtained. The obtained product was purified by sublimation at 320° C. under 4.0×10−6 Torr for 2 hours and 450 mg of a deep purple amorphous solid was obtained.

Workup

  1. stirringthe obtained mixture was stirred for 10 minutes
  2. customThe formed precipitates
  3. customwere separated by filtration
  4. washwashed once with ion-exchanged water, once with a saturated aqueous solution of sodium disulfite
  5. customThe washed precipitates
  6. customwere dried
  7. temperatureunder heating at a reduced pressure and 0.84 g (the yield: 51%) of a light purple solid of 8,15-bis(p-biphenylyl)benzo[a]pentacene
  8. customwas obtained
  9. customThe obtained product was purified by sublimation at 320° C. under 4.0×10−6 Torr for 2 hours

Sources & evidence

ORD record
ord-aa907a7fc89748ba9a82338fba49a31d
Source dataset
uspto-grants-2002_12
Patent number
US06489046B1

Reaction notes

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