Hydrochloric Acid → Dibenzo[fg,qr]pentacene

HRID 347602

Reaction equation

HRID 347602 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1C=CC=CC=1>[CH:2]1[C:3]2=[C:8]3[C:10]([C:9]4[CH:14]=[CH:15][CH:2]=[C:3]5[C:8]=4[C:7]2=[CH:6][C:5]2[CH:4]=[CH:5][CH:6]=[CH:7][C:4]5=2)=[CH:11][C:12]2[CH:13]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]3=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 113099-BromophenanthreneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 136023Dibenzo[fg,qr]pentaceneYield 3.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 9-bromophenanthrene (50 g) in benzene (250 mL) was added solid aluminum chloride (50 g) gradually in portions. After the addition was complete, the mixture was heated at reflux for one hour, then cooled to ambient temperature. A slow addition of 2N HCl (250 mL) was then made (caution: exothermic). The resultant mixture was heated to reflux for an hour. Once cooled the mixture was filtered. The crude solid was washed with several portions of water and air-dried. The black solid (13.5 g) was placed in a soxhlet extractor and extracted with hot THF. The concentrated extracts were sublimed under a nitrogen flow at 300° C. and 640 mTorr to provide 1.2 g of dibenzo[b,k]perylene. The sample was pure by HPLC analysis (Keystone PAH, 5 micron, 100×3 mm).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureat reflux for one hour
  4. temperatureto reflux for an hour
  5. temperatureOnce cooled the mixture
  6. filtrationwas filtered
  7. washThe crude solid was washed with several portions of water
  8. customair-dried
  9. extractionextracted with hot THF
  10. customat 300° C.

Sources & evidence

ORD record
ord-e67260151475429cb05449b56e7e20f6
Source dataset
uspto-grants-2007_02
Patent number
US07175922B2

Linked notes

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