Potassium Carbonate → Benzo(g)chrysene

HRID 2405449Notes

Reaction equation

HRID 2405449 reaction equation
COC=CC1C=CC=CC=1[C:11]1[C:12]2[C:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[CH:24]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2.C(=O)([O-])[O-].[K+].[K+]>CS(O)(=O)=O.ClCCl>[CH:20]1[C:19]2[C:24]3[C:11]([C:12]4[C:17]([C:18]=2[CH:23]=[CH:22][CH:21]=1)=[CH:16][CH:15]=[CH:14][CH:13]=4)=[CH:14][CH:13]=[C:12]1[C:11]=3[CH:24]=[CH:23][CH:18]=[CH:17]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 72332051HCID 72332051, compound

Product 1

HCID 9140Benzo(g)chryseneYield 25%

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A reaction vessel was charged with 24.0 g of 9-[2-(2-methoxyvinyl)phenyl]phenanthrene and 100 mL of dichloromethane. 6 drops of methanesulfonic acid were added to the mixture using a Pasteur pipette at room temperature with stirring. The mixture was stirred at room temperature for 8 hours. After completion of the reaction, 100 mL of a 10% potassium carbonate aqueous solution was added to the mixture. After removing the aqueous phase, the organic phase was washed with water and a saturated sodium chloride solution, and dried over magnesium sulfate. After removing magnesium sulfate by filtration, the organic phase was concentrated. The residue was purified by silica gel column chromatography to obtain 5.21 g of the target benzo[g]chrysene (yield: 25%).

Workup

  1. customat room temperature
  2. stirringThe mixture was stirred at room temperature for 8 hours
  3. additionwas added to the mixture
  4. customAfter removing the aqueous phase
  5. washthe organic phase was washed with water
  6. dry with materiala saturated sodium chloride solution, and dried over magnesium sulfate
  7. customAfter removing magnesium sulfate
  8. filtrationby filtration
  9. concentrationthe organic phase was concentrated
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f5a5577109b545d988c20ae99d6dd778
Source dataset
uspto-grants-2014_08
Patent number
US08803420B2

Reaction notes

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