Potassium Carbonate → Benzo(g)chrysene

HRID 2274128Notes

Reaction equation

HRID 2274128 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 48.4%

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

24.0 g of 9-[2-(2-methoxyvinyl)phenyl]phenanthrene and 100 mL of dichloromethane were placed. 6 drops of methanesulfonic acid was added by means of a Pasteur pipette while stirring at room temperature. The stirring was conducted at room temperature for 8 hours. After completion of the reaction, 100 mL of an aqueous 10% potassium carbonate solution was added. An aqueous phase was removed, and an organic phase was washed with saturated saline and dried with magnesium sulfate. After filtering off magnesium sulfate, the organic phase was concentrated. The residues were purified by silica gel column chromatography, whereby 5.21 g (yield 25%) of benzo[g]chrysene as an intended product was obtained.

Workup

  1. additionwas added
  2. customAn aqueous phase was removed
  3. washan organic phase was washed with saturated saline
  4. dry with materialdried with magnesium sulfate
  5. filtrationAfter filtering off magnesium sulfate
  6. concentrationthe organic phase was concentrated

Sources & evidence

ORD record
ord-182b80f30d8e44bcb8ff334fcd3d48c5
Source dataset
uspto-grants-2015_09
Patent number
US09126943B2

Reaction notes

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